The Real Estate Game Has Changed — Here’s How the Pros Still Win Artwork

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Freedom Fighter Podcast

The Real Estate Game Has Changed — Here’s How the Pros Still Win

November 04, 2025 • Season 1 • Episode 62

0:00 | 1:12:37

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The path to true freedom in real estate isn't always a straight line—it’s about knowing when to pivot, when to partner, and how to stay sharp in an ever-changing market. This week, we're cutting through the noise to bring you the real lessons learned from 20 years of navigating the ups and downs of real estate. We share candid insights on adapting your strategy, building crucial relationships, and the "light bulb moments" that transform a solo journey into a thriving ecosystem of success.

We discuss how to approach lenders as an opportunity, not a plea, and why understanding their perspective can be your biggest competitive advantage. We explore the unexpected challenges that come with scaling, the importance of balancing reinvestment with personal draws, and how "shiny object syndrome" can actually be a gift when managed wisely.

📌 Key Topics:

✅ Adapting to Market Shifts: How to thrive when the real estate tide goes out, and why a strong business model is key.

✅ The Power of Storytelling in Finance: Learn why banks are looking for your story, not just your financials, and how to build those crucial relationships.

✅ Strategic Delegation & Partnership: Discover when it's time to let go of responsibilities and leverage others' strengths to scale your business.

✅ Cash Conversion Cycles: Understand how different real estate strategies generate income at varying intervals and how to stack them for continuous wealth.

✅ Self-Management vs. Professional Management: Our take on when to manage your properties yourself and when to hand them over to a professional.

✅ Mentorship & Continuous Growth: How we stay sharp and grounded, even when at the "top of the food chain."

✅ Succession Planning for the Next Generation: Our philosophy on teaching financial literacy and fostering independence in our children.

Join us as we pull back the curtain on the behind-the-scenes realities of real estate, offering actionable insights to help you build lasting wealth and freedom.

00:00 Navigating Life Changes and New Ventures

06:03 Real Estate and Market Adaptations

12:04 The Importance of Storytelling in Business

19:58 Building Meaningful Banking Relationships

23:46 Understanding Lending Limits and Participation

27:38 Learning from Mistakes in Real Estate

31:28 The Challenge of Shiny Object Syndrome

32:55 Transitioning from Flipping to Other Ventures

33:51 The Evolution of Real Estate Strategies

34:46 The Impact of Market Conditions on Flipping

35:41 Finding Joy in Real Estate Deals

36:40 Scaling Real Estate Businesses

37:36 The Growth of Liquid Lending

38:25 Breaking Through Financial Ceilings

39:25 Opportunities and Challenges of Scaling

40:17 Leveraging Time and Skills

43:27 Understanding Cash Flow and Investment Cycles

46:12 Navigating Real Estate Management

51:23 Staying Grounded and Seeking Mentorship

55:40 Memorable Deals and Lessons Learned

57:57 Self-Managing vs. Professional Management

59:49 The Journey to Delegation

01:01:13 Understanding the Value of Time

01:02:40 Learning from Experience and Mentorship

01:04:36 Light Bulb Moments in Business

01:06:33 The Importance of Partnership

01:07:31 Navigating the Financing Side of Real Estate

01:11:15 Planning for the Future

01:14:09 Philosophy on Succession Planning

Oh, and welcome. You've been in the real estate game for a little bit now and you've seen hundreds of investors come and go since you've been doing this last 10, 15 years.

Ryan Miller (08:58)

What do you think separates the ones who build real freedom from the ones who just stay chasing their tail? think belief. They the ones that typically dip out are ones that, you know, they maybe got in during a hot time in the market. So say any time in the teens, basically up to probably what? Twenty one, twenty two. Anybody that existed in real estate during that time probably made a pile of cash, right? Because you just needed a house. didn't have to be the right house. Right. So inventory was more important than buying the right deal, I think.

Owen Audio (08:58)

Ryan Miller (09:28)

The ones that got out when it got hard are the ones that had a business model that didn't adapt to stress in the market. So what we're seeing right now is you try to underwrite a deal with 7 % debt. It doesn't pencil it. because sellers haven't adjusted their pricing to accept that people aren't willing to buy it for what they want to actually sell it for because they're used to 20, 21 pricing. So I think it's belief in your systems and having the ability to withstand the punches. And I think a lot of people that

Owen Audio (09:28)

Ryan Miller (09:57)

really got active during those times ⁓ when the music stopped. They're like, what do do now? Because the way that they were generating cash income, you know, cash flow went away. And if you didn't have another business or another source of income to supplement everything that you had going on in real estate, washed out a lot of people. You know, it's the whole adage of the rising tide lifts all ships when it goes out and you see it who's swimming naked. A lot of people are naked. Yeah. ⁓

Owen Audio (09:57)

Ryan Miller (10:25)

So I got in right at the tail end of that in 22. It was one of my first ones. So I was going through the education when everybody's like, Oh, in 21 was this is great. And then 22 came and I hit the ground running pretty fast. And then the brakes fell off or the brakes locked up. And I was like, Ooh, this is a different than what I've been reading about and learning about and stuff. So it's been a lot slower than the, you know, 23 and 24 has been a lot slower, but.

Owen Audio (10:25)

Ryan Miller (10:55)

I had to pivot and it actually goes back to something you asked me years ago. You asked me basically a question of.

Owen Audio (10:55)

I had to pivot and it actually goes back to something you asked me years ago. You asked me basically a question of.

Ryan Miller (11:05)

you asked what do you what do you plan on doing when the cash runs out this kind of framework of where how you asked it and I was like what do you mean like I'm just gonna burrow out all this stuff and it's gonna be good like I don't know what you're asking so like for me it was like I didn't know what you meant I mean I do now but at the time I was just like you just burn and then it's free cash perpetual motion machine yeah just you you get it going and it just once you get the the machine going it never stops so

Owen Audio (11:05)

Ryan Miller (11:35)

But yeah, it stopped pretty quickly after that question. You know, the thing is, though, I can't say that I maybe wouldn't have done something similar if I had started at a different time. I got got started in 2005. So that was right before the great financial crisis. Everything, you know, was then that was bad. So what we're seeing right now, to me, I'm kind of like, I mean, everyone's like, ⁓ seven percent like the interest rates are so high. And I'm like, that's exactly how they were when I got started. Like my first mortgage was seven percent.

Owen Audio (11:35)

Ryan Miller (12:04)

And I did an 80, 20 alone. So I had a 7 % mortgage and a 9 % mortgage, right? And that because they were liar loans back then you can basically sign your name and fog a mirror and you can get a loan. But, ⁓ so it's all relative to when you start. So if you got in and the teens and everything was just going like this, and even like the later part where everything was hockey sticking, then now it's kind of more like just, you know, steady eddy type of an environment. Interest rates are kind of just hovering around the same mark. It's much.

Owen Audio (12:04)

Ryan Miller (12:33)

tougher to operate, especially if you're used to the easy times. I just got done with a book called Quit. you ever read that one? It's a phenomenal one. It's basically about knowing when to move on and when to give up. what I like about what you said is during the teens, when you have a tailwind, everyone's going to do well. Just doing real estate, you're going to make some kind of money. But then when that headwind comes, the ones who are able to withstand that are the ones that are actually going to gain altitude.

Owen Audio (12:33)

Ryan Miller (13:03)

And I mean, there's many things that I've had to pivot on, like my strategy and when I got started in 2020 is not at all remotely like what it is now. But I don't see the 7 % as a reason not to do real estate, just to change the strategy. Like I'm maybe going into deals putting 30, 40 % down, whereas before I was a little money as possible. And my house mortgage, I have a 2.5 % interest rate. I will never sell that. I have no desire to refinance it.

Owen Audio (13:03)

Ryan Miller (13:32)

the strategy for that meets the interest rates where it was at. So I think that knowing when to pivot is being knowledgeable about how to operate in those environments. And because you started in the 7%, it's almost like you're implementing a playbook of like, know what to do when this happens. So what other bumps and bruises as far as the lending environment has changed your philosophy and how you invest now?

Owen Audio (13:32)

Ryan Miller (13:56)

I think right now, if you know how to put a deal together that will work for you and you can articulate that to somebody that's selling a property and your reason why and you can understand their motivations, I think that leads to a lot more productive conversation with putting something together rather than just writing a blind offer and asking them to finance 100 % of the deal. think mutual understanding with your sellers, if you can get in front of them,

Owen Audio (13:56)

Ryan Miller (14:26)

You can have a lot more productive conversation because you can describe what's going on with them, right? They, they know it too. You know, like, Hey, I get it. You probably don't want to sell because you have a low interest rate or maybe they, maybe they're really motivated, but they just want to hang onto that price because they're used to 2021. but I think if you talk about what's going on at a macro level and then bring it back to, okay, what does this mean to you? What does it mean to me? How can we make this work together? I know you don't want this asset anymore, but you'd also don't want to give it away. Is that fair? And then, you know,

Owen Audio (14:26)

Ryan Miller (14:55)

you can have a productive conversation with it. But the lending environment right now, I think, you know, I have a little bit of a cheat code since I have a ⁓ hard money business and I've learned a lot more about financing in the last five years since we've been operating that. So and I've made so many more connections. So to me, I have a little bit of an advantage over somebody that's just maybe used to dealing with one bank or a couple of banks. And they're like, well, they said, no, I guess I'm out now. I'm kind of like, OK, I heard no from them, but I know they may be overweight and.

Owen Audio (14:55)

Ryan Miller (15:23)

the type of loans that they have out there. Cause every bank is different, right? Especially smaller ones. They may get really overweight and say multifamily or maybe they have too many ⁓ types of one project that they're doing. And the bank committee is going to be like, look, we're way overweight here. There's a lot more risk and they want to de-risk their loan portfolio by concentrating in other areas. So just because they said no to you doesn't necessarily mean they don't want to ever do business with you. It's just the timing.

Owen Audio (15:23)

the type of loans that they have out there, because every bank is different, right? Especially smaller ones. They may get really overweight and say multifamily, or maybe they have too many ⁓ types of one project that they're doing. And the bank committee is going to be like, look, we're way overweight here. There's a lot more risk. And they want to de-risk their loan portfolio by concentrating in other areas. So just because they said no to you doesn't necessarily mean they don't want to ever do business with you. It's just the timing.

Ryan Miller (15:50)

And so that was something that I have learned more about in the last five years is how the financing and the back end of that works and how banks actually look at projects because we have to look at it the same way. Being an asset based lender is a little bit different than, you know, just a mortgage lender that needs a FICO and, know, all your tax returns and pull your pants down and show me all your financial statements and everything. Like it's a little different, but that's very similar because the deal has to make sense. The borrower has to have a good, ⁓

Owen Audio (15:50)

Ryan Miller (16:18)

head on their shoulders and know how to execute on a business plan. And then we can suss out the rest of the details, right? But I think the connections have been something that has been really helpful for me. And I see that as a true competitive advantage. And the way that you approach lenders is you're inviting them into an opportunity. And I always advise clients. I worked when I was doing bigger pockets leads and people, was getting three, four phone calls a week where I was just mentoring people on how to get started.

Owen Audio (16:18)

Ryan Miller (16:47)

And that's what I would tell them is when you're approaching a lender, you're not begging for money. Like when you're younger and you're getting your first car loan, you're like, hey, I make money. Can you give me money? Please help me, sir. Exactly. It's your begging. But when you're bringing investment opportunities, the exact same thing, all the banks work on a risk premium. And they might say that multifamily, they're putting a 300 basis point spread on the five-year treasury. They're willing to take on that much risk.

Owen Audio (16:47)

Ryan Miller (17:14)

If they're over leveraged and they have too much C-class multifamily, they'll say, okay, we'll do it at 400 basis point spread, but that's why the rates don't work for that one. And so I would say go to five different lenders, see what all of them will do, put them on a spreadsheet. Some of them might say, we'll do a 20 year note, some will do a 15, you know, and you just move all the pieces and see them. When you put them on a spreadsheet, you can see what makes me the most money. And doesn't mean that it's a bad deal, it just, they don't want to do the deal.

Owen Audio (17:14)

Ryan Miller (17:44)

I had a really interesting coffee meetup last week. did you go, I can't remember if you went to that Ryan. So we had, there was a new bank that I started working with and a council of bluffs called mid, mid States bank. And I got to know the president or the regional VP. I'm not sure what her title is. Everybody's a VP at a bank, but I was dealing with a couple of people that are commercial lender and then more on the executive level. They came to my meetup and

Owen Audio (17:44)

Ryan Miller (18:10)

They started following me on social media, which is a little like I'm like, I'm out on social media quite a bit. And some of the stuff I post is really random. I'm walking through terrible houses and whatever. So I'm like, how's the lender going to look at this? But they're super cool. then anyway, they came to the meetup, right? And we probably had, I don't know, 20, 25 people there. And it was super interesting because we got to hear we got to ask them questions that you don't ever get to ask them when you're going in to try and get a loan. Right. So you're talking about a project and they're like, OK, we have to take committee.

Owen Audio (18:10)

Ryan Miller (18:38)

and all those things. And so we got to ask them like, what is your committee actually meet about? Like, do you guys know about this already? And you guys are just getting ready and having a beer on Friday. You know, I mean, like, that was the conversation. Illuminati. Yeah, exactly. No one's ever seen it. So we got to like pull back the curtain on what they actually talk about and what what rang ⁓ what I really took away from that was they want to hear a story.

Owen Audio (18:38)

Ryan Miller (19:01)

They don't want to just have your financials and click through a bunch of Excel spreadsheets and look at your tax returns and then make a decision. They want you to sell them. Like, why is this deal going to work? Why are you bankable? Why should my company take a risk on you? And that was really interesting to me. So I've always been a big fan of story selling, right? You can articulate something in a way that's entertaining, but also get the message across. It goes so much further than just like bullet points on an email or a spreadsheet, right?

Owen Audio (19:01)

Ryan Miller (19:31)

And so that was really fun conversation, but looking kind of behind the curtain on how banking decisions are made, they're people too, right? If they, they're like, man, you know, Tanner had a rough go the last couple of years, but I really believe in him and he has a really good story. And I think based on his track record and his drive and determination, he can execute on this plan. think we can take a risk on it. But if you're just sending that in blind and trying to shop for the lowest quarter point, you know, reduction in rate that you can get, I don't like that approach at all.

Owen Audio (19:31)

Ryan Miller (19:58)

I like the relationship one, where you go in and you spend time with them, you find out what are they looking for as a banker. And that's important too. So I don't think they get asked that a lot. It's more of like, what can you do for me? Not, how can we work together and make this mutually beneficial? Who can I introduce you to? What type of loans are you looking for? Because we all know business owners, right? We're all in real estate and entrepreneurs and whatever. So we kind of rub elbows with those types of people. Those are good referrals for banks. And so the outcome of that was like, I know

Owen Audio (19:58)

Ryan Miller (20:27)

You know, Dane Peterson, he's like, hey, I'm going to call, you know, I'm going to call Chris or Darrell that attended the meeting. And then a couple other people are like, Hey, can you give me their number? And I'm like, that's awesome. I like, so they came to the meeting and it was super helpful for everyone, but it also helped them out. So that's why you can't do that from behind a computer. know, how do you find that ladder? So you go to a bank and go for commercial loan. You know, you go to the vice president of land, the commercial lending. And so you think that's a person like.

Owen Audio (20:27)

Ryan Miller (20:56)

Not just a entry level analyst was basically what they are. But like in your head, you see vice president of commercial lending and you think they're pretty high up, but in reality they have 20 bosses above them to get to the executive level. how do you climb that ladder to get to the executive level? Because the larger you go, the higher it goes up in the food chain as far as the committee and the higher the buy-off. So how do you your story? I guess more precisely.

Owen Audio (20:56)

Ryan Miller (21:26)

to that higher level when you're at a gatekeeper? I think it becomes a lot easier with age and experience. That's the first thing. So me being 50 years old, I may be dealing with a VP in air quotes that's 30. so odds are I probably know a lot more than that person does just based on my lifespan. So I think you get comfortable with getting referred higher when you have more of a mutual age.

Owen Audio (21:26)

So I think

Ryan Miller (21:54)

It's challenge for somebody that's 25, right? To go in and they see a VP level and they're like, I'm young. You feel intimidated by somebody that's older than you and more experience has the title. But I think referrals go a long way. So the more you can network with people and connect with them and get buy-in, the more comfortable they're going to be in referring you to their banking relationship. So I think referrals is number one.

Owen Audio (21:54)

Ryan Miller (22:19)

Number two is my favorite banks to deal with are the ones that have one branch two branches, maybe three small town banks Regional banks. I don't like dealing with US Bank Wells Fargo I've never have right so the ones that operate more like a family ⁓ owned business are the kind of small town banks, right? They they like relationships. They want you to come in they they like the story all their members are farmers Yes. Yes, that's how I've got I grew my whole business

Owen Audio (22:19)

Ryan Miller (22:48)

by using small town banks and small regional banks. think, you know, like between two of them that I did a ton of banking with until I kept bumping into their legal lending limit and I had to go elsewhere. There were one bank had two branches, the other one had one and it was my hometown bank. And the owner of the bank was my assistant baseball coach in high school. Yeah, like my family still lives there. He's literally known me my whole life. So that was easy. So I had an advantage there obviously, but yeah, I think

Owen Audio (22:48)

Ryan Miller (23:17)

So to bring it all back, think when you get more experience, it becomes easier. Obviously, when you have connections, that makes it so much faster and easier and dealing with so many less layers than a huge bank. That's the way to go when you're trying to break through and get financing on your first deal or maybe your first couple of mentioned something that I don't think most people realize, but banks, smaller banks especially, have a legal limit on how much they can land. Yep. And so you just think this

Owen Audio (23:17)

Ryan Miller (23:46)

Bank just has this endless, uh, you know, pot of money, but that's not true. Like the smaller bank you go to, you might only be able to pull a million dollars or two million dollars or something like that. And loans from them. then you have to go into the next bank. So, know, it's crazy though, like this, this small bank that I was dealing with, I, and their legal lending limit for one person or any entity that you're a member of. you can't like game the system by like,

Owen Audio (23:46)

Ryan Miller (24:12)

Surprise, I'm over here in this LLC now. It's not me. You know, you can loan to me. They have, know that, right? So they have to deal with bank examiners that come in and look at all their books. So they audit their files. And if you have a loan that if you're dealing with a small town bank and you, and you have a big, you know, let's say you have an $800,000 loan on a million dollar loan limit, that's going to pop out, right? So they're going to look at your file and odds are they're going to go through it and probably ask a lot more questions. But I think the interesting thing I learned too is yes, they have a legal lending limit and it's based on their deposits.

Owen Audio (24:12)

Ryan Miller (24:42)

Right. So banks can loan out, I think, what is it? Nine bucks for every dollar they have on deposit in the bank. it's a I mean, it's a huge snowball effect. And so banks, small banks, a lot of times will look for other small banks that they can acquire just to get their deposits so then they can continue growing because it's a nine X multiple on that. And the other interesting thing I learned, I didn't know this until, I don't know, probably seven, eight years ago. Banks do participation a lot more than anyone realizes.

Owen Audio (24:42)

Ryan Miller (25:10)

And what I mean by that is basically if you get to a point where you're ⁓ maxing out the amount of loans you can take out of a bank, that bank, they want to continue doing business with you. They can call other banks and they typically will have a short list or a network and they'll say, we have $500,000 worth of loans. Here's the borrower and they basically give them your bio. Now the bank that you're dealing with, not the new bank, but the bank you're dealing with, they're going to continue servicing the loan.

Owen Audio (25:10)

And what I mean by that is basically if you get to a point where you're ⁓ maxing out the amount of loans you can take out of a bank, that bank, they want to continue doing business with you. They can call other banks and they typically will have a short list or a network and they'll say, we have $500,000 worth of loans. Here's the borrower and they basically give them your bio. Now, the bank that you're dealing with, not the new bank, but the bank you're dealing with, they're going to continue servicing the loan.

Ryan Miller (25:40)

It just goes on somebody else's books and you may not even know that's happening. So you see that a lot of times in more like Fanny Freddie type origination loans where owner occupants are going to get FHA or whatever. Those loans get sold all the time. Like you may start out with, you know, U S bank and it may go to Mr. Cooper and then it may go to Wells Fargo. And you're like, I just got another random bank statement in the mail from this bank. I've never heard of them. They're like, Hey, surprise, we own your loan now. Send it, your money to us. It's just weird.

Owen Audio (25:40)

Ryan Miller (26:08)

And all this stuff happens behind the scenes. And I don't think, you know, people that get in the lending or banking industry just don't know because there's no reason for you to, but there's a lot of machinations that happen behind the scenes there that it's really interesting to learn about. It's a banking is one thing. I, I think they make it obscure on purpose. I, ⁓ you're talking about the 25 year old banker, like you walk in there and they're like, yeah. So things will go up about 25 BIPs.

Owen Audio (26:08)

And all this stuff happens behind the scenes. And I don't think, you know, people that get in the lending or banking industry just don't know because there's no reason for you to, but there's a lot of machinations that happen behind the scenes there that it's really interesting to learn about. It's a banking is one thing. I, I think they make it obscure on purpose. I, ⁓ you're talking about the 25 year old banker. Like you walk in there and they're like, yeah. So things will go up about 25 BIPs.

Ryan Miller (26:38)

What's a bill? They make up these words instead of just saying 0.25 % interest, our basis points. They just make more obscure so that you can be, we're gonna make it as convoluted as possible so that you don't understand what we're talking about and we'll just take your money. I found the same thing. And I know you guys did too with the military, right? There's always acronyms for everything and nobody else that's not in the military probably knows what a lot of them are. And that was the same. worked for IBM for quite a while.

Owen Audio (26:38)

Ryan Miller (27:08)

And they have the same thing. It was just always alphabet soup. there were everybody's thrown out all these acronyms. And the minute you start talking to somebody that isn't working there, they're like, what are you talking? What are you talking about? Yeah. So it's a lot of explaining. I really like what you're saying about storytelling. Cause I, I've found more success with putting together a portfolio. Here's my personal financial statements, statement, real estate owned. Here's, you know, examples of cashflow, but people like to just give a highlight reel. They show everything's always been perfect and I'm awesome. But when I show,

Owen Audio (27:08)

Ryan Miller (27:38)

here's some mistakes that I've made and this is how I've corrected it. So it's not going to happen again. They're a lot more receptive because they're like, okay, I mean, he's responsible. It's not just, he got lucky on a few deals. It's he's actually taking the steps to fix things. I had this really, really cool breakout session. I went to a BP con here, what three, three, four weeks ago in Vegas. And there was a named Brian Burke that was talking and he's a

Owen Audio (27:38)

Ryan Miller (28:06)

really well-known syndicator in multifamily real estate. And so he started as, I think he was a cop or a firefighter originally, had a bunch of firefighter or cop buddies. And basically his first few deals, he pitched them and they all wanted to be involved in real estate, but they hadn't done the homework like he had. And they trusted him he's a good dude. And he started putting deals together and grew and grew and grew and grew and always did a good job with, I'm sure he had some hiccups, but he's known as a really good operator.

Owen Audio (28:06)

Ryan Miller (28:34)

He was in this room, right, with two other. It was Kathy and Rich Fetke and then Brian Burke. And they both were pitching their latest deal that they were raising money for. Brian's was a pivot off of what he normally did, which was multifamily. And he was going to do senior living and not converting senior living into multifamily. talking like buying and operating a senior living facility or building one ground up. And what he did was he aligned he aligned with four

Owen Audio (28:34)

Ryan Miller (29:04)

major operators in that space and said, do you have the ability to staff this if we build it? Here's the facility. Here's the scope, whatever. So he basically developed partnerships with them in the room. They had a limited partner, guy that had done over 100 deals. So he'd put him put money into all kinds of different projects. And they gave basically him the opportunity to tear apart each of their pitches. And then at the end, he said, thumbs up or thumbs down, I would invest with you today.

Owen Audio (29:04)

Ryan Miller (29:34)

And it was really cool to see the back and forth with that because you got to hear the story and then you got to hear all the tough questions. Cause normally it's just like pitch fest and you don't hear what happens afterwards. But he was like, it was just a great back and forth. And then they opened it up to the audience. So everybody kind of got to ask the hard questions. My favorite interaction of that whole thing was Brian Burke gave his pitch. He did a really good job. He's very articulate, articulate, controlled the stage. And then the guy asked him, said, okay,

Owen Audio (29:34)

Ryan Miller (30:02)

You've never done one of these before. Why should I invest now? Why don't I wait until you've had a proof of concept and have two, three of these under your belt before I put my money in with you? He thought about it for second. He had a great answer. And he said, the reason is if you look at my entire track record of being involved in real estate deals, I have tried something new this time, this time, this time, this time. And he had a whole bunch of examples where he tried something new.

Owen Audio (30:02)

Ryan Miller (30:32)

Not related to multifamily, not related to senior living, but he executed on it and it went well. was a success. So he said, you're betting on my track record of being able to figure something out that's new to me, but I know how to operate the rest of it. So I know the people, the players and the process. And that is what is going to make this successful. And he was, and the guy like, you know, the LP sat back and he's like, you know, that's a good answer, you know? So I was just like, that was a really cool interaction that you don't get to see very often.

Owen Audio (30:32)

Ryan Miller (31:01)

of a peek behind the curtain. how do you balance being able to scale your real estate business with all these other opportunities versus just staying in what you know and what's worked? Yeah, well, my problem a lot of times, problem, gift, whatever, is I have a little bit of FOMO and I have a lot of bit of shiny object syndrome. So I've always...

Owen Audio (31:01)

Ryan Miller (31:28)

Here's my deal. So if I get really interested in something, I get obsessed and I, I study it. I read about it. I listened to podcasts. I, I talked to people. go deep, right? And it's to the detriment of other areas of my life. And so I was so obsessed with real estate when I first got started in it, that that's all I did for a while. And I learned everything that I could at the time without before social media, before YouTube, before all that. And, ⁓ but I think

Owen Audio (31:28)

Here's my deal. So if I get really interested in something, I get obsessed and I, I study it. I read about it. I listened to podcasts. I, I talked to people. go deep. Right. And it's to the detriment of other areas of my life. And so I was so obsessed with real estate when I first got started in it, that that's all I did for a while. And I learned everything that I could at the time without before social media, before YouTube, before all that. And, ⁓ but I think.

Ryan Miller (31:57)

balancing your question was more around like how do you balance the shiny object? I like it more now because I get bored doing the same thing over and over again. If I was just a guy that owned a business that did plumbing or trucking or whatever, and I would get bored. I would get bored after a while and I would have to have somebody handling the day-to-day stuff because I've always been a hunter and I don't like managing.

Owen Audio (31:57)

Ryan Miller (32:27)

Like I like finding deals. I'm good at it. I'm good at dealing with sellers. I'm good at the conversations and everything. I'm not, I'm a good director. I'm not a good manager. I just don't want, I don't want to deal with the drama and the people and the problems and everything else. That's why I like finding deals. I like buying deals and I hate real estate after that because everything sucks. It's like you're dealing with problems all the time. And I'm kind of like, if I have somebody that can handle that or an interference, I'm happy. But if I have to deal with the day to day, it just drives me crazy.

Owen Audio (32:27)

Ryan Miller (32:55)

and then I'll probably move on to something else. I think that was one of our first conversations when I met you. I mean, everyone has no in story, but when I was, when I was in a station in Minnesota and I just learned about bigger pockets, I listened to all the podcasts when I bigger pockets, I was like, all right, I'm moving to Omaha soon. Like I'm gonna start reaching out who's out here. And Owen came up and I messaged him. It was probably something like a, Hey, what's a real estate, you know? Like, and he was super welcoming and, and um,

Owen Audio (32:55)

Ryan Miller (33:22)

our first conversation, I was like, so what do you like about real estate? like, I don't, hate it. If I could make money without having to do real estate, I would. But ⁓ I eventually got licensed and I have my core clients that buy a lot of deals with me and were exclusive. And then I'll find deals and I'll pitch them to people in the network. But I know that I will never have exclusivity with yourself or other people because you're looking for opportunity everywhere and you don't tie yourself down.

Owen Audio (33:22)

Ryan Miller (33:51)

But I found a deal in Fremont when I was stationed in Fremont and I brought it to Owen. I don't know if I ever told you this story. And he came up and walked it and it was a multifamily good deal. It penciled well. And so we submitted an offer and they came back and wanted proof of funds. And his answer was Google me. Tell them to Google me. Oh my God. That's embarrassing. He walked towards his car.

Owen Audio (33:51)

But I found a deal in Fremont when I was stationed in Fremont and I brought it to Owen. I don't know if I ever told you this story and he came up and walked it and it was a multifamily good deal. It penciled well and so we submitted an offer and they came back and wanted proof of funds and his answer was Google me. Tell them to Google me. Oh my God, that's embarrassing. He walked towards his car.

Ryan Miller (34:17)

You turn around. That sounded really arrogant. I'm sorry. didn't mean that. That's my favorite on story. That's pretty good. I forgot about that. Oh, that's such a douchey thing to say. Here we are. You have, uh, you've pivoted, guess, more, more shiny objects, if you will. Like when I first met you, you were wholesaler, flipper, stuff like that. You've kind of let that. I remember a couple of years ago, you've made a comment. I think I'll always flip.

Owen Audio (34:17)

Ryan Miller (34:46)

It kind of like in your blood, but now you've, can't say you, I don't know the last time you've done a flip. Are you still doing them or? Yeah, I have one going right now, but definitely I'm not looking for them. It's more of like five, one fall in my lap and it makes sense. Yeah, I'll do it. but yeah, I kind of let that die on the vine a little bit just because, ⁓ well, a it's tougher now, much tougher. ⁓ it's, know, there's a lot more price reductions. ⁓ it's

Owen Audio (34:46)

It's kind of like in your blood, but now you've I can't see you. I don't know the last time you've done a flip. Are you still doing them or I have one going right now, but definitely I'm not looking for them. It's more of like five, one fall in my lap and it makes sense. Yeah, I'll do it. But yeah, I kind of let that die on the vine a little bit just because ⁓ well, a it's tougher now, much tougher. ⁓ It's you know, there's a lot more price reductions. ⁓ It's.

Ryan Miller (35:13)

The interest rate environment makes it harder. People don't want to sell. People aren't willing to accept lower pricing. It's just a weird time. don't think I don't remember since I've been doing this for 20 years. I don't remember anything that's been exactly like this. It's always a little bit different. Each market is a little bit different, but this one's just tougher to operate a flipping business in and unburned out. Like I've done so many of these, probably 300 plus flips over the years that I just don't like, I don't get any.

Owen Audio (35:13)

Ryan Miller (35:41)

Do I like making the money? Yeah, it's great. Do I like finding the deal? Do I like negotiating it? Yes. Do I like everything after that? No, I don't like dealing with inspection request or inspection addendums, doing all that stuff, managing contractors, just the whole thing. So I got, I just got tired of the grind and I'm kind of more cherry picking like who I want to do a deal with. What deal do I want to do? Do I want to try development redevelopment? Those are kind of, so I'm kind of getting to do the shiny object thing without having to be so like crazy busy and flipping. Cause we know we were doing

Owen Audio (35:41)

Ryan Miller (36:10)

When it was kind of at our peak through probably 08 through, I don't know, 2012 or 2022. No, I got those wrong. I'm old. 2018 through about 2022, we were doing between three to five a month. And that's and we didn't have any staff. It was it was managing crews like me, managing the lead flow. I handle marketing. We kind of divided and conquered one business partner in that. And then that we made a lot of money. I mean, we

Owen Audio (36:10)

Ryan Miller (36:40)

We made a lot of cash and that was my, you you live your job, right? I left a, you know, six figure job in 2017 to do real estate full time. And I had to, I had to generate income, right? My wife got laid off what less than six months after I left my job and she was making about the same thing I was, if not more. So I was like, Oh boy, now I got a 250 K hold a dig out of just to be scratch with what I was before. So it's like, I had to make some moves and I knew how to do it.

Owen Audio (36:40)

Ryan Miller (37:10)

But long-winded answer to your question is, yeah, I'm not definitely not flipping as much or as intentionally as I have, but I will still do it. So what are you looking at more now as you mature in your, in your real estate golden years? ⁓ I, I really, tell you what, man, I, ever since we started liquid lending, which was in 2020, ⁓ that's it's been so five years now.

Owen Audio (37:10)

Ryan Miller (37:36)

And that business has grown and grown and grown its hockey stick over the last five years. And we've gotten a lot more capital. We've done a lot more deals. We've got more borrowers. We've gone to different markets. And that is what's cool is because I get to look at and kind of participate in all these deals and some really crazy and cool ones that we've done that I probably.

Owen Audio (37:36)

Ryan Miller (37:56)

that I maybe I would have looked at at one time, but I'm like, I don't want to do that. Now I kind of get involved, but I don't have to do all the hard work. Yeah, exactly. Yeah. And we could say, you know, we get to hear the stories and whatever and look at all this. then, so I like the fact that I'm able to kind of like keep my knife sharp by learning new things still, even though I've been doing this, you know, I'm kind of an old dog in real estate here at 20 years, but this lending business has kind of rejuvenated me a little bit because I still get it. Like, you know, I can talk to all these people and borrowers and I have something they want and

Owen Audio (37:56)

Ryan Miller (38:25)

they have something I want so we can we can find kind of a mutually you know, beneficial conversation and and the deals man, I just love deals. I remember the the $1 million net worth threshold. It seemed like it took forever to break through. I was and breaking through that it's one to five is pretty quick, but there's a ceiling at every there's a 5 million mark, a 10 million mark and the same is true in business. You know, you obviously have business partners in that. But what what have you found?

Owen Audio (38:25)

Ryan Miller (38:55)

that was unexpected with each ceiling that you've broken through. example, in the trucking, I thought that I could use QuickBooks to process money. Turns out when you process $50,000, they flag it because it's an irregular activity. And so then they froze my money for three weeks. And that was something I didn't expect, but I wouldn't have known that if I wasn't transferring large funds. So what have I learned? That breaking through each threshold that with the scale comes more problems.

Owen Audio (38:55)

Ryan Miller (39:25)

Yeah, with a scale definitely comes more problems, but I think with the scale comes a lot more opportunities too, because people, if you start getting a little bit of recognition and a little bit of experience in getting deals closed, that's who brokers want to work with, right? They want sellers and brokers, they want somebody they know is going to close. They want certainty. So when you're getting more and more deals under your belt, you get the experience level and you start getting a little bit of not notoriety, but recognition for that, I think it gets easier there.

Owen Audio (39:25)

Ryan Miller (39:52)

You deal with different problems, right? And the problems have another zero or two zeros on them than you're used to dealing with. So I always tell people like, get, you know, I meet with a lot of newer investors and the biggest thing is like, well, they can't wrap their mind around, you know, doing a deal where you're going to make, you know, a hundred thousand, $500,000. And those happen, right? But I'm like, look, it's all relative. You know, when I, I was where you are right now, 20 years ago.

Owen Audio (39:52)

Ryan Miller (40:17)

and $5,000 seemed like an enormous amount of money. mean, that represented, you know, 40 hours of my time. And that's how I always looked at it was back then. was like my time translates to X. And so if I'm spending this many hours or if I'm making this much money, that represents this much of my time, but shifting that into leveraging not just, you know, money, but people and finding it realizing, think for me, a lot of it came when I started acknowledging what I'm good at, what I'm not.

Owen Audio (40:17)

Ryan Miller (40:46)

And when you're really honest with yourself, because everybody has an ego, right? That you carry around and you think, oh, I'm good at everything. And you have kind of this facade you put up, but like, I know what I'm not good at now. And I'm perfectly fine acknowledging the people that are way better at it than me and involving them. If they can show that they can handle something, I have a hard time letting things go until somebody proves that they're adept at handling whatever the problem is. If they can prove that.

Owen Audio (40:46)

Ryan Miller (41:09)

I don't want anything to do with it. Like do your thing. You know what I mean? So I think when you, when you start getting bigger, you start getting out of the, being a solo, a solopreneur, which is really, really hard because you have to put on your marketing hat, drive leads, and you got to take off your marketing hat and operate it and get it sold or whatever. And then you're like, Oh crap, I forgot to market. So then you got to start all the way over. Right. It's just hard to find that good, you know, continuous improvement because you're trying to do so many things with so many people. Let's try cooking for eight kids or.

Owen Audio (41:09)

Ryan Miller (41:37)

What are you having? Seven, sorry. Yeah. But you know what mean? So like, think the, the higher up you go when you absolutely that first million bucks in net worth, I mean, it's, it seems like it's never going to happen. You look at your, you know, year over year spreadsheet on your PFS and it's like, I'm $50,000. And it's like, how many $50,000 is, I have to make to get to a million? That's a lot, but then compounding interest takes over principal pay down if you're buying rentals and then

Owen Audio (41:37)

Ryan Miller (42:06)

you know, the market appreciation does its thing and it doesn't take as long as you think. mean, when you got what 20 or 75 % leverage or 80 % leverage on, on stuff and the market's done what it's done, you look pretty smart, pretty fast. And so I think when you, when you're in the right timing can really accelerate your net worth, ⁓ you know, breakthroughs, but you can still do it. I mean, it's just time.

Owen Audio (42:06)

Ryan Miller (42:29)

I think everybody you get into this business and you have to get it 10 years. I think there's so many people that made a lot of money really fast when the market was really good that they had a false sense of what actually was real. But I think you got to do it 10 years. Otherwise, you're going to set yourself up for ⁓ markets that are just going to crush you when they go sideways. And I think time is the most important because that's that's the biggest freedom that we're all fighting for. And what you said earlier about moving away from the flipping, it sounds to me like that's a time problem because

Owen Audio (42:29)

Ryan Miller (42:59)

the time as you achieve more scale and your portfolio gets bigger, the time it takes you to generate another hundred thousand means you got to do four, four or five flips or you do one multifamily. And so I think that that's the biggest thing with scale is granted with the multifamily comes other problems. If you're doing a single family and make a 5 % mistake, you lose two grand. But if you're doing a multifamily, make a 5 % mistake, that's 500,000. Well said. Yeah.

Owen Audio (42:59)

Ryan Miller (43:27)

I ⁓ was talking with Ryan before we recorded and we interviewed a guy named Ian Ziegler, ⁓ whose actually his episode is going to drop tomorrow. ⁓ But he had a really interesting take on this. We were talking about basically that you have to eat, right? You can't eat equities. So you get involved in real estate. I think, Ryan, back to your point when you and I had that talk and you said, well, what do mean? You know, everybody goes broke eventually.

Owen Audio (43:27)

Ryan Miller (43:53)

You get the premise, right? Everybody that's involved in real estate investing, you keep dumping your money back into deals and you can't eat equity. So you gotta have something that's gonna pay your bills. And I think that's a lot of times too what washes out the people who are involved in this business is, it was easy when you were borrowing everything and you could borrow out hundred plus percent of your deals and maybe you flip here and there and you can make a really good levy. make a couple hundred, 250 grand, 300 grand. And then it gets harder and then you're like, ⁓ man.

Owen Audio (43:53)

Ryan Miller (44:22)

Now I can't pay the bills. So you got to have something else going on that's going to generate that stuff. The nice thing about real estate is there's so many different offshoots of investing to generate cash. You need property management. can broker, can syndicate, can do all these things to generate chunks of cash. But what Ian said was there are cash conversion cycles. And I'm like, what do mean by that? And he said,

Owen Audio (44:22)

Ryan Miller (44:46)

Flipping, you got about what, four to six months? That's a cash conversion cycle. It's a chunk of money. And then if you spread that out over a year, you do a few of those, there's your yearly income. And then a bigger deal, maybe it's gonna take a couple of years to buy and reposition a multifamily. Then you refinance it, put agency debt on it. And then that's a money event. That's a cash conversion cycle. That's a two-year cycle. And then you looked at, maybe you get into a deal where it's a longer hold time. You're projecting five to 10-year hold, depending on market conditions. That's a longer cash conversion cycle.

Owen Audio (44:46)

Ryan Miller (45:14)

But if you start stacking those, they're just going to start happening like over and over and over again. Yeah. It's yeah. It's like a money bomb going off. It's just how quickly is it going to happen? How short the fuse is and all that. One of the clips I was said I did and on the podcast, I saw them out. Basically the same thing. Like if you just buy single family houses, put each one on a one year thing, pretend the first one's paid off. You can just refinance it, get your money out and then

Owen Audio (45:14)

Ryan Miller (45:43)

kind of live off from that. And I don't know if people just thought I was an idiot or like what, but tell them it's your cash conversion cycle. Like that's basically what I was saying in that. And you just refinance it and people are like, dude, you're your most viewed video. was our most viewed people like tore me up and like telling me I'm an idiot and this, that and the other, it's basically exactly what you're, you're saying there. Like you just, you don't make any money on the first 15 years, but you can start to live off from it after a while.

Owen Audio (45:43)

kind of live off from that. And I don't know if people just thought I was an idiot or like what, but tell them it's your cash conversion cycle. Like that's basically what I was saying in that. And you just refinance it and people are like, dude, you're your most viewed video. was our most viewed people like tore me up and like telling me I'm an idiot and this, that and the other, it was basically exactly what you're, you're saying there. Like you just, you don't make any money on the first 15 years, but you can start to live off from it after a while.

Ryan Miller (46:12)

And I'll tell you, I've been, you know, this is my 20th year doing this. So 2005, I started to 2025 now. It's super weird to now be the age that I am because I don't think like I don't walk around thinking like, oh, you're 50. Like I don't feel that way at all. I still feel like 1990 was 10 years ago. It's really weird. And then people are like, oh, sir. And they're like, I'm like, what do you know? Don't call me, sir.

Owen Audio (46:12)

Ryan Miller (46:39)

I look in the mirror and there's a harsh reminder, but ⁓ no, think it's really okay. I don't know how to quite to put this, but when I was reading all the books, when I first started trying to learn all this stuff, podcasts, books, whatever, right? Anything I could read, bigger pockets. People would talk about, ⁓ you can, to your point, you buy one of those a year for 10 years, and then you can start harvesting that equity after 10 years go by. And then you just do it the next year with a different property and so on and so on.

Owen Audio (46:39)

Ryan Miller (47:09)

Right. And I'm like, that sounds amazing and financial freedom. In my head, I was always like, all right, and set myself up for later. This is later Owen. And I'm I'm living it now. It's it's I will say it is pretty awesome because like I have paid down so much on a lot of these that I've held for a long time where I can I can sell them. Maybe I just want to de you know, declutter and get rid of some of my single families, which I've done, I think, three or four sales this year, single families where I have one hundred thousand one hundred fifty thousand in equity.

Owen Audio (47:09)

Ryan Miller (47:37)

I mean, that's pretty sweet. Now, granted, I'm going to get kicked in the balls at tax time. But Sam's going to be happy for you. know. But I did time it because this year I have a gigantic cost seg that we're going to be doing that I that should wipe out a big chunk of that. So that's kind of my my behind my mouth. Just did my first one. Nice. Yeah. It's like roughly a quarter million dollars in cost savings. That's awesome. Yeah. Yeah. That's real money, too. That's crazy to see when the straight.

Owen Audio (47:37)

Ryan Miller (48:06)

The first multifamily we bought the straight line was like $50,000, but the cost seg was like $600,000. It's like insane. Yeah. Yeah. I tell you what does suck though is when you sell one that you cost seg and also I'm selling, I'm, the process of selling one that I did a 1031 exchange into after doing a 1031 exchange before that. So I have like a domino effect and then I did a cost seg. So yeah, this one's gonna get a probably hurt capture.

Owen Audio (48:06)

Ryan Miller (48:32)

Yeah. So that's the, that's the thing that, you know, the, the unsexy part of it. I always got to pay the piper. So you mentioned like when you still got bills to pay. So how do you discern when to take a draw and when to keep reinvesting? Cause that's, that's a trap that I keep falling in is I just want to reinvest. And, know, my wife's like, why are we putting 150,000 into this house, but we need carpet at our house. I,

Owen Audio (48:32)

Ryan Miller (48:56)

can't depreciate the carpet. The cobbler solar and have no shoes. Yeah, exactly. Yeah. so that's a good question. I think it's a highly variable on, on what your life is like, right? How much, how much money you have, but I think, you know, if, if we're keeping it all on the, know, on the same starting line, it, I have right now. ⁓ okay. So when I, when I was operating my flipping business, that paid the bills. That was my day to day money. We travel money, you know, kids, whatever all that.

Owen Audio (48:56)

Ryan Miller (49:25)

That's how we paid the bills. When that has kind of dried up, right? So that's, you know, call it two, 250 and income, you know, depending on the year could be a little more, little less. That's a lot of money and that's no longer coming in. But I started the lending business, you know, five years ago and that's eclipsed that. ⁓ So the question is, how do I decide when to distribute or when to reinvest? The lending business is not real estate, but it's tied to real estate. So I, all my money is active income off there.

Owen Audio (49:25)

Ryan Miller (49:55)

Right. So it's a partnership and then we distribute based on ownership percentages and we typically will just let that money build up. And then, you know, when we're like, Hey, I could use it. Could use a, and we'll see, we all basically collaborate on that and say, okay, yeah, we're going to distribute X. So we were doing a pretty good clip there for a while where we do monthlies, but you have to kind of look at the, at the projections and the year and how things are tracking and all that. That's the lending business. But I think it's, it's with anything where you have income coming from ⁓ stuff to pay other bills as opposed to like, don't.

Owen Audio (49:55)

Ryan Miller (50:25)

I don't draw a dollar out of my rentals. Like I've owned this property that I was talking about, but I have the cost seg and the 10 31s. I haven't taken one dime out of that account in 4.6 years. So yeah, I guess leaving it if you can make smart decisions on what you're putting it back into and don't blow it on stupid stuff. Right? Anybody that's listened to us this long tell that you've been successful in real estate. And I would say in our

Owen Audio (50:25)

Ryan Miller (50:54)

Circle if you will everybody like you said earlier, everybody has no one story everybody like They flock to you at the meetup. So whatever, you know, you're involved with the Ria. You're on the Ria radio podcast ⁓ You're active in ⁓ Collins. Well, I guess he doesn't do it anymore, but you were at Collins ⁓ Meetup you kind of took that over and made it into your own Thursday morning ⁓ coffee meetup so anyhow, my point is saying that is people

Owen Audio (50:54)

Ryan Miller (51:23)

flock to you and try to try to get to know you. How do you stay? I mean, nice two point question. How do you stay grounded in that? And then also, how do, where do you go for mentorship outside of that? Cause if you're at the top of the thatch line, you have to go somewhere else. Yeah. ⁓ that's a good question. ⁓ how, so how do I stay grounded with, is I want to make sure I understand though, are you, are you asking like, how do I not get a big head? Yeah.

Owen Audio (51:23)

Ryan Miller (51:52)

Well, everybody tries to run to you. Here's OK. I'll tie it back to this. So I my like jobby job that I had for a long time, my W-2, I was in recruiting. So I did for several different Fortune 500 companies, ConAgrifoods, IBM, Rico Americas, Compact Computers. I worked for all of them. I was an agency headhunter for a while, too. I got really comfortable interviewing people. So I did literally thousands and thousands of interviews over the years, hired thousands of people.

Owen Audio (51:52)

Ryan Miller (52:18)

And I liked that. liked interviewing and finding out people's stories. So I would always, if I ever sit down one-on-one with somebody, they always have a story to tell. doesn't matter who they are, how any experience they are or whatever, I'm to get it out of you. And so I have a natural tendency to just interview people and I get, I'm like zeroed in on their story when they're telling it to me. I'm not like distracted with it. And that's kind of into my detriment sometimes. Cause a lot of times I get wrapped up in conversations where I'm like, Oh my God, it's like 30 minutes later was not planning on this.

Owen Audio (52:18)

Ryan Miller (52:48)

But I finally figured out, cause we've, guys talk about, know you're deep thinkers and we've talked about how do you find your why and finding your why and it gets thrown around all the time. Like, I think I kind of have mine figured out and mine is more around, it's not the business, the money, the real estate success, you know, being, having a podcast, all that. Fine. That's, that's all fine. But that's not why I'm doing it. Like I couldn't care less about my, I'm like, I, this is a nice ⁓ hoodie.

Owen Audio (52:48)

Ryan Miller (53:18)

The rest of them I have are like $5. You know what mean? Like I don't, I don't buy stuff. don't want to dress enough. that's my nicest hoodie. You know what I mean? So, but like I don't do it for the status or the fame or any of that. I just do it because I love it. And I love meeting with people that are trying to figure it out. And if I can help you shortcut by telling you all the stuff I screwed up on and, at least, you know, kind of like reach down and pull you over, over the hump here and, and, and help you on your way.

Owen Audio (53:18)

Ryan Miller (53:46)

That's what I love, man. so I look, I look, can I, can I go to a coffee every day a week with somebody? No, I can't. My schedule is different now where I can't accept as many like one-on-one meetings and all the social. So I kind of have to pick my battles with that. I love the bang for the buck that you get out of having a meetup, a small meetup. I feel like those are my favorite places to operate. Um, but yeah, so the answer, the first part of your question, and I forgot the second, because I've been rambling. Where do you.

Owen Audio (53:46)

Ryan Miller (54:15)

We're being at the top of that food chain. Where do you go for? How do you keep sharpening your skills? Yeah. So the benefit of being involved and having a podcast and interviewing people of all different skill and experience levels and net worth and all that is I've learned something new from every single one of them that comes on. So I have a

Owen Audio (54:15)

Ryan Miller (54:40)

cheat code to mentorship and that I don't actually have to do a formal mastermind or whatever. But I've had 250 episodes. I've interviewed 250 people. That is awesome. Like every single time I've learned something and I've like, yes, I'm cheesy and I read, listen to some of them, but I like to hear what I missed because I'm so like generally locked into that conversation that you kind of forget after a while. But so that's one thing. But then the second thing is the more deals that I've done with partners, I meet their

Owen Audio (54:40)

Ryan Miller (55:10)

friends, their connections, people they've done business with, and that has been kind of like a natural level up with the way they operate. so, yeah, you know, the partners I have seven business partners in different entities and businesses, and they are all super smart and they all have different skills and abilities than I do, and they all have different network than I do. So being ingrained and getting the opportunity to just kind of live in their ecosystem, that's a cheat code.

Owen Audio (55:10)

Ryan Miller (55:40)

What's the favorite deal you've done? Mmm.

Owen Audio (55:40)

What's the favorite deal you've done? Mmm.

Ryan Miller (55:45)

Ooh, that's a good one. ⁓ man. I would have to say I had an awesome whole tail one time where we made about 110,000 and we owned it for like a week and then we just cleaned it. So that was a pretty cool deal. That was in like a happy hollow area. So.

Owen Audio (55:45)

Ryan Miller (56:06)

Yeah, all got beers after that. Yeah. Yeah. Yeah. I bought everybody, everybody drinks or whatever, wherever we were. That was the eclectic one. I was kind of a little different. Yeah. Yeah. And they have like an attic above the attic that had like a ton of square footage that was like, I didn't even go up there. I didn't realize anymore. Yeah. So that was the good times. Um, and then I don't know, I like, I've had other deals where like, okay, I bought the fifth Avenue hotel that got converted into apartments, right? In the eighties.

Owen Audio (56:06)

Ryan Miller (56:36)

And I bought that deal historic building. That was a super, have so many stories about that place. Like everything from mall top cocktails to like a naked dude in the lobby, making a gingerbread house with a steak knife. ⁓ like I've had a crack head break into the storage room and pulling, pulling everything out of their air conditioners appliances. ⁓ The elevator would just randomly open into a, ⁓ the penthouse apartment where people were staying. Yeah.

Owen Audio (56:36)

Ryan Miller (57:02)

So like I have stories for days about that place, but I probably learned as much as I have on any other deal that I've owned by buying that property. So I have a little bit of a special place in my heart for that deal. But I also just sold my very first rental property that I ever had. you know, so I owned it for 20 years and I just sold it. So I kind of have a little.

Owen Audio (57:02)

Ryan Miller (57:27)

Yeah, no, not at all. Actually, I thought I didn't know how I was going to feel. I knew I would feel some kind of way about it. But after the dust settled and I was like, you know, got my six figure check out of that, I was like, I don't have to worry about that anymore. I don't have to deal with attendance calling and whatever. So that was ⁓ yeah, that was that's probably another you always remember your first. No, no. Do you think that people should start their real estate careers, self-managing or getting professional management to handle it? Self-managing. And I would debate anyone on that. Yeah.

Owen Audio (57:27)

Ryan Miller (57:57)

You don't know what you're paying for if you don't know what's actually involved. And the only way to know what's involved is to deal with the phone calls, to deal with the leasing, to deal with all that stuff. Now, I will say, I think you should self-manage, but I also think you need to be 100%. ⁓ You need to know as much of as possible about the landlord tenant law and the state you're operating in. ⁓ Because you can get in some hot water with discrimination, with inconsistent app processing of applications, all kinds of stuff like that. So know your stuff, but do it yourself.

Owen Audio (57:57)

Ryan Miller (58:27)

Eventually when you get to a point where, I don't know what you guys think about this, but I think there is a magic number of doors that you can handle when you're working a W2. And I think it's 20. I got to about 20 and stuff's really started falling apart. So maybe it's a little bit for them, but I think it's between 15 and 20 that you can handle. can manage no problem. Beyond that, it starts getting stressful, especially if they're like single families. So you have 20 different addresses, 20 different roofs.

Owen Audio (58:27)

Ryan Miller (58:55)

you know, sets of tenants and all that. think it's a little more. That's how I started. But ⁓ yeah, I think that's, ⁓ I think everybody should self manage. And then when you get to a point where you understand it, you know what you're paying for, then get referred to the right property manager for you. I had this similar type of question for my men's group. We were both in a Christian men's group separately, but I brought ⁓ concerns. said, I need to look for my next hire for the trucking company and

Owen Audio (58:55)

Ryan Miller (59:22)

I need some kind of metrics to decide, should it be a bookkeeper, should it be a dispatcher, should it be an operations manager? How do I discern when I'm ready to do that? And I was hoping that they'd say, okay, when you have six months of reserves and this, that, and the other, and then they said, well, when you're stretched thin, then you'll know what you need. I hated that answer, but it was probably the one that I needed at the moment because I found that bookkeeping is not my strong suit.

Owen Audio (59:22)

Ryan Miller (59:49)

dispatching I'm good at, it takes my time away from other things. So those are my first two hires. And I think what you're saying is when you get stretched to that capacity, you'll know that you're ready for a manager. Yes. Yeah. And I, I gave it a test run with a guy that was kind of in my ear about turning my portfolio over to him. So I had about 20 and I'm like, look, I don't want to, I've worked so hard to build up all this cashflow by self-managing. I'm saving so much money by doing it. And you know, it's going to, cause I was like, you know,

Owen Audio (59:49)

Ryan Miller (1:00:19)

buy enough rentals where your monthly income exceeds your expenses and then you can replace your income and you're free, right? Time freedom. Quit your job if you want. But I looked at 20 of them and I bought those and rehabbed them and leased them and did all the things. And then I was making like two grand a month, know, whatever three grand a month. And I'm like, I can't, I can't retire from this. And meanwhile, I'm having kids and my expenses are going like this. So I was just like, he's asking for you to give him. Yeah, So I'm now I'm chipping away at the money that I worked so hard for.

Owen Audio (1:00:19)

Ryan Miller (1:00:47)

So what I did was I turned over, I'm like, look, start with one. So see what, show me what we can do here. He had at least in like less than a week and it was probably for a hundred and 150 bucks more than I probably would have advertised it for. So he literally paid for itself. And I'm like, my, I'm so dumb. So that was a big light bulb moment for me. And then I started kind of turn over more as they became vacant. I would just kind of transition over to them and have them handle the leasing. And I was just like, this is the way.

Owen Audio (1:00:47)

Ryan Miller (1:01:13)

And then I got freed up to do more, but I don't think I would have been positioned to make that decision unless I would have got, you know, gone through the gauntlet of 20 of those. ⁓ it's probably different for everyone, but I would highly suggest anybody that's getting started self-manage. I think because I like metrics, I think that there is a tangible number to that and whatever that is for the individual. But if you have 20 units all renting for about a thousand dollars a month, that 10 % fee that you would pay a manager, like you said, equates to two or three grand.

Owen Audio (1:01:13)

Ryan Miller (1:01:43)

If your time is worth more than that three grand, then it makes sense to hire a manager because then you can do 20 more. And I think that's the metric that makes the most sense. And I tell people, break down your calendar, do the 15 minute increment drill. You you look at where all your time's going and then assign a dollar per hour to each one of those tasks. Checking your email is a $5 an hour task. So every time, if you value your time at a hundred dollars an hour, every time you're checking your email, you're losing $95. And so when you frame it that way,

Owen Audio (1:01:43)

Ryan Miller (1:02:12)

then it's much easier to delegate and feel like you're gaining rather than losing. And that's the gap in the game. If you're only looking at, I'm losing this 10 % per month, then yeah, I mean, you're always going to be thinking that you're taking a loss hiring a manager. So why'd you ask the men in the men's group if you knew the answer? Well, sometimes you need, and that's, that's part of why I like that group is, is I'm the youngest in my group. like 20 years. Like everyone in there is, is in their 50s, 60s.

Owen Audio (1:02:12)

Ryan Miller (1:02:40)

and they've been running businesses. And so just hearing how they operate, because I mean, I saw, what are those, GIFs, GIFs? We can debate that later, GIF. Yeah, so I saw one of those where they showed the top 10 companies of all time. you know, when IBM and everyone's cycling, and there has never been a company that's been in the top 10 consistently for, I don't remember if it was like 10 year period, but they showed it for the last 100 years.

Owen Audio (1:02:40)

Ryan Miller (1:03:09)

how they're always cycling. And so I believe that a company that is still operating after 20 years are doing something right. And if I can figure out what that one thing is from them, one thing from them, then I can implement those in my business. Even if I think I know the answer, I want to hear what works for them. Yeah, I was thinking back while you were talking to the kind of the darlings of the business world from a company perspective. And, know, in the late nineties or like around 2000, it was like Microsoft GE. You never hear

Owen Audio (1:03:09)

Ryan Miller (1:03:39)

When's the last time you heard something about GE? Like they were like a blue chip, blue chip company, Jack Welch, you know, the accolades went to him kind of like Warren Buffett. But yeah, you don't hear anything about them anymore. Microsoft is kind of like it also ran now. It's like, yes, it's annoying. I have to have windows. you ever seen the rise and fall of Sears? Oh, no. If that's a story or a book I haven't read it. No, no, it's I'm just saying that they're back story. Yeah. Yeah. How Sears blew up from the 80s into the 90s and, know, it was all retail and then at

Owen Audio (1:03:39)

Ryan Miller (1:04:07)

as the fall shopping malls came and everything, they got into more finances. I can't remember the whole list of their subsidiaries, but they bought some really big household name companies and they chose to exit those companies to pursue this dying retail business. That was part of the book Quit. Interesting. I want to know more about light bulb moments. I really like those because it just shows that we're constantly growing and there's constantly things

Owen Audio (1:04:07)

Ryan Miller (1:04:36)

We're always trying to uncover the unknown unknowns because the known unknowns, it's I know I can go find a book and improve the skill set, but the unknown unknowns is when you get into a new venture and something happens, you're like, that's how that works. So what are some other light bulb moments that you think were transitional in your career? Yeah, I think a big one was the property management light bulb. Another one was, you know, I did this for 12 years before I left my W-2. So I was I was working

Owen Audio (1:04:36)

Ryan Miller (1:05:06)

you know, 40 hours a week at my W2 and then at nights and weekends, I was out looking for deals, working on projects, painting, you know, all that stuff. So I probably had about a 60 hour ⁓ window there where I was really busy and then I had two young kids and a wife and I'm trying to manage all that. it's not, wasn't, you know, it stressful. It was what I wanted to do, but ⁓ I wish I would have probably done things differently there. ⁓ But I would say another

Owen Audio (1:05:06)

Ryan Miller (1:05:34)

major light bulb moment was the first time I really considered partnering and how that could affect the landscape of what I was trying to accomplish. the fact that I was so you get to a point where like, okay, I did it for 12 years. And if you're doing something that most people are unwilling to do for 12 years, you start to kind of feel maybe pride and like, I it's a badge of honor that I've worked my butt off this long and for so hard. And

Owen Audio (1:05:34)

Ryan Miller (1:06:03)

your pride gets in the way a lot of times of what actually, you know, makes sense for you to do to get out of your own way. And that's what was a big light bulb moment for me is just like, I'm not good at everything, even though I'm trying to portray that I am. I'm really not. And so what I met, ⁓ you know, Brandon was my first business partner with a red ladder, our flipping business. And we dated quote unquote for about six months before we kind of pulled the trigger and decided to both leave our careers and go full time into this. And then.

Owen Audio (1:06:03)

Ryan Miller (1:06:33)

After that, I was like, you mean I don't have to do all of this stuff that I'm normally used to doing. It was just super weird. It was a weird adjustment, not having control over everything. But once he proved that he was adept at doing those things, I was like, I'm such an idiot. Why? Why did I hang on like grim death to all these responsibilities when I could have just found the right person and had them do stuff probably way better than me. So partnering was property management at first, partnering second. And then the

Owen Audio (1:06:33)

Ryan Miller (1:07:02)

light bulb moment for me when I learned about ⁓ the financing side of real estate, not just that. that wasn't that was more of a process, not an event. But going through that, really, the light bulb came on for me on how I can operate differently and look at deals differently and borrowers and just how to structure things and work with the people. And everybody brings something different to the table. So I don't know. That's just been really cool for me to just partnering with people. And I learned something new every time.

Owen Audio (1:07:02)

Ryan Miller (1:07:31)

And odds are they do so many things better than me that I can then adopt what they're doing and just blatantly rip it off. And it's for the benefit of both of us. So those are kind of some big ones in business. I would say the irony of the HR guy hiring people who's afraid to partner and hire people to replace us. Yeah. I was a lone wolf for 12 years. Yeah. And it was lonely, man. I remember

Owen Audio (1:07:31)

Ryan Miller (1:07:57)

You know, when I, like I said, you know, YouTube wasn't around, there were no podcasts. There wasn't much in this way. Social media, bigger pockets wasn't around yet. I found this message board. was looking for something, anything, any way to connect with somebody. Cause like when you're involved in this, if you, and I'm kind of weird, so I read a lot and not all my friends did all the people that I knew from developing relationships over the years, went to college with them, maybe hung out the bars, whatever, played baseball. didn't invest in real estate. They didn't have the, that.

Owen Audio (1:07:57)

Ryan Miller (1:08:27)

thing that made me do things that other people weren't doing. Like I can't stop it. You know, it's just like you need somebody and after like 30, 45 seconds, you can tell if they got it. You know what mean? There's that, that something that they have where you, you're not going to accept your reality. You want something better. And I just could not find that commonality with my existing group of friends. And there's no opportunity on my space.

Owen Audio (1:08:27)

Ryan Miller (1:08:52)

Yeah, that my space, I tell you what, pre my space. I remember this when I found my space, somebody had told me about it whatever. finally got on there, created my page and then they went bankrupt like immediately after that. I was just like, well, that was fun. then, but ⁓ no, when I ⁓ when I started like desperately searching for information online, I finally found this and it was ⁓ it was called CRE online. It was this dude out of Colorado, if I remember right. And it was basically a message board.

Owen Audio (1:08:52)

Ryan Miller (1:09:21)

It wasn't even a forum. It was just like random messages and you, and I read everything on there because it wasn't big, but there was a lot of good stuff negotiating to put deals together, financing, blah, blah, blah. And I was like, what else is out there? And so I just start, kept Googling, Googling, and then finally came across bigger pockets in 2007 or eight. And I was like, my God, these are my people. Where have you got, where has this been? And so that was just a whole different, that was a light bulb moment for sure. ⁓ but I'm

Owen Audio (1:09:21)

Ryan Miller (1:09:48)

You know, and then I remember this kid, hundred of y'all on there. Right. Right. I remember this kid. was thinking about this on the way out here. There was, we were, we were talking about meetups, right? So we have the coffee meetup, you know, um, and then we have a couple of bigger meetups in town and then the West Oh and the Lincoln one, there's all these meetups, but there wasn't really anything like that in 2006, seven, I joined the local RIA here and there were six members, seven members, something like that. went, her in an olive garden.

Owen Audio (1:09:48)

Ryan Miller (1:10:17)

Right? Like once a month and all garden on 72nd. And, you know, fast forward to this, this guy that I met on bigger pockets, same as you, I was looking for anybody local and there wasn't very many, there was like three or four dudes. Matt Swiss helm was his name. had no idea what he's doing now, but he's younger kid, younger than me. And he's like, Hey, I was thinking about putting a meetup together. You want to meet at Noly pizzeria. And I was like, I don't know where that is, but I went.

Owen Audio (1:10:17)

Ryan Miller (1:10:46)

met him, there were probably 15, 12, 15 people there. And I was like, this is cool. And we started talking. I'm like, man, I wish this was a regular thing. And then he was like, yeah, he did one more and then that was it. And then it was like dead air until Colin started his meetup and whatever year that was. So, um, yeah, that was joining meetups was another light bulb moment for me. Before, uh, we'll let you go before my dog dog tears down the door.

Owen Audio (1:10:46)

Ryan Miller (1:11:15)

What we've talked about, you've been successful, all that stuff. What is the next chapter of freedom look like to you? I guess kind of put a different take on what we normally ask people, but what's the next 20 years look like? What do you keep searching for? Yeah, think, you know, I'm trying to think about this realistically because like, you know, like I mentioned, I'm 50, right? Am I going to continue buying deals up till the day I die? Maybe. ⁓ But I'm looking at things now from

Owen Audio (1:11:15)

Ryan Miller (1:11:45)

Mike, I have a daughter that's a junior. You guys both have kids that graduated, right? And so I have a junior that's coming up. That's going to be a big change when she's out of the house. And I have a 13 year old that's got probably five more years in the house. So I'm like, well, what does that mean? And I have aging parents, right? So my parents are 79 79 and 78. And my wife's parents are even older than that. And I have an 87 year old mother-in-law, right?

Owen Audio (1:11:45)

Ryan Miller (1:12:11)

things are going to look dramatically different. And rather than try and plan out my next 20 years, I just have to I'm looking at like, OK, I want to enjoy as much time as I can with my my parents and my kids while they're still around. And I want to not be so bogged down in everything that I'm doing that I have to do for work that I can't on a random Friday just say, you know what? I'm going to go watch my daughter's volleyball game or I'm going to go do this and that.

Owen Audio (1:12:11)

Ryan Miller (1:12:41)

So I want to be mindful of my time. ⁓ I try not to do any meetings on Fridays at all, other than the podcast. And I just try to manage my calendar so that can do a lot more freedom. Big picture, what I want to do. I still want to do deals and I want to probably do ⁓ some more development work. So I have a piece of land and Council Love Center contract that's like 22 acres. We're doing all the like... ⁓

Owen Audio (1:12:41)

Ryan Miller (1:13:09)

city planning meetings, TIFF, know, entitlements, those type of things, you know, environmental. Those are cool and different and new. And that's not just the same same like how another house flip or another multifamily property or whatever. So I want to keep doing different things still within real estate. But I want to like I just love the people I work with, Like despite me wanting to strangle them and probably vice versa on a day day basis, they're great dudes and and and gals. And they make me better.

Owen Audio (1:13:09)

Ryan Miller (1:13:39)

So I just want to do cool stuff with cool people and be able to dictate my calendar to an extent and spend time with my family and do the stuff I enjoy. What's your philosophy for succession planning? Like setting your kids up? What do you believe about that? OK, so I think about it like this. I ⁓ came from a family that was that my parents, my dad worked hard.

Owen Audio (1:13:39)

Ryan Miller (1:14:09)

and my parents were both entrepreneurs, they gave me the belief system that I didn't think there was anything I couldn't do the whole time I was growing up. I was always really motivated, a nerd, and really competitive. And so I got into sports, baseball specifically, really dialed into that. And I really grew up with the belief that I just had belief in myself. And I was like, think I can do anything I set my mind to.

Owen Audio (1:14:09)

Ryan Miller (1:14:38)

And that came from my parents. They didn't have any roadblocks or any, you know, baggage that they carried from how they were raised that they put in front of me that said, you, should be realistic. You shouldn't do this. So I just had this belief where I was like, I can do anything I want. I just have to figure out what that is. Cause I didn't know what I wanted to do when I grew up. Still don't. ⁓ but succession planning, ⁓ I, I figured it out. I got student loans when I went to college. I got to send up,

Owen Audio (1:14:38)

Ryan Miller (1:15:06)

tried to get as many scholarships as I could. did all the essays and all that. ⁓ But I had to get student loans and got those paid off and I survived and I figured it out and I struggled. And I don't want to give my kids a silver spoon where they're going to not have to work or just have a life on easy street. So I want them to be able to struggle and figure their own way. ⁓ But I also want to give them more, give them some tools to get there and teach them about business and real estate.

Owen Audio (1:15:06)

Ryan Miller (1:15:36)

And if they choose to go that route, maybe they want to work with me someday. Great. I'm not going to force it down their throat. ⁓ But they, you know, we talk about money all the time in the house. When I say all the time, like that's not the focus, but I mean, we don't restrict our financial conversations. We talk about what things cost. And my older daughter has gotten really good at like recognizing what her time for money is. And does she really need that thing that she wants to buy? Because she knows she's going to have to work.

Owen Audio (1:15:36)

Ryan Miller (1:16:06)

to get it. And so we pick and choose basically on what they're what they spend money, their own money on. Like we'll pay for food. And I made a deal with my kids a long time ago. I will pay for books whenever you want to buy them. I don't care if you want to buy them as opposed to go to the library. Yes, you could say that's maybe a better lesson. Go to the library. But they're one of their favorite things to do always was go to the bookstore. So I loved going with them because I'm a lifelong learner and I want them to enjoy the same thing. But when it comes to succession planning.

Owen Audio (1:16:06)

Ryan Miller (1:16:33)

Um, I don't want to give them everything like the keys of the kingdom, but, um, there'll be money and a trust, um, probably when they're 25, they'll be able to, you know, get access to a chunk of that. Obviously we're going to pay for, um, some of their college. I still think they need to pay for, uh, some of it as well to appreciate what they're doing and not major in underwater basket weaving. You know what mean? I want them to go into this with their eyes open and say, I'm ready for life. Um, I'm not, I don't have this huge safety net, but, you know, we're going to support them and, and.

Owen Audio (1:16:33)

Ryan Miller (1:17:03)

provide, but also I want them struggle. So they can figure it out on their own. One thing that we've been testing out is, you know, our kids, we try and involve them in everything we can. They're, they're doing demo work at flips. They're mowing lawns. They're, know, like now with the trucking company, my son does the dispatching. So I pay him a commission for that, but what we're trying, I don't remember whose video we saw, we're keeping a log of all of their commissions and all the pay if we're paying them flat rate hourly, whatever. So they know exactly what they're getting paid.

Owen Audio (1:17:03)

Ryan Miller (1:17:32)

but they don't get that in cash. They're at the end of the year, we're going to take that dollar amount and then we're going to tell them you can go take this money, invest it into the stock market. You can invest it in one of our properties. You can invest in our businesses, but you can only spend the distributions you get from those investments. So if you put in the stock market, you can spend the dividends. You can't spend the principal. And so just showing them that snowball effect, they were, they were, ⁓ at the dinner table last night, kind of going back and forth like,

Owen Audio (1:17:32)

Ryan Miller (1:18:00)

We can't actually touch that money. But I think that in the long run, it'll pay off and they'll see the fruits of it. Yeah, I like that. We recently got ⁓ the Venmo card, like that. So you can load it with what they can load with money. You can load it with money and then they have to make choices. Right. It's not just like, Hey, mom, will you buy me this? Hey, dad, we buy me this. They have to be like, OK, how much is on here? You know what I mean? And tying all that back. But my kids are also a little I don't know. I don't know what

Owen Audio (1:18:00)

Ryan Miller (1:18:30)

The current kids that are in like junior high and high school are, I can only operate off of what I know with mine, but they have no interest at all in AI, none. Like they give me a hard time about it. You know, like, did what did you say? GPT say dad. And I'm like, you guys should really pay attention to this. This stuff is moving really fast and it's not going away, but I don't know. I feel like sometimes I just want to go analog again, man, and just ditch the cell phones and exist how we used to my wife that earlier for the other day.

Owen Audio (1:18:30)

Ryan Miller (1:18:59)

I just want to throw this thing away and never say it again. So I like it from the computer aspect. hate it from a phone texting, all that stuff. Someone watched this and stuck around to the end and want to get a hold of you, especially their local meetup. Is that your best way to go to your Thursday? Yeah, yeah, I love that. yeah, caffeine and cap rates. It's every Thursday at 10 a.m. at Sozo coffee house 1314 Jones Street.

Owen Audio (1:18:59)

Ryan Miller (1:19:28)

So we have a meetup there. usually it's any topic. So we talk all about real estate business partnerships, financing, you name it. It's a different jukebox of ⁓ topics. I'm also on Owen Money Real Estate. That's my handle on Instagram. So you can always find me there. Ria Radio. We've got our podcast. It'll be on Spotify and all the stuff. So that's usually the best. So summary, Google me. me. That's so embarrassing. Well, we don't have a fancy sign up.

Owen Audio (1:19:28)

Ryan Miller (1:19:57)

Maybe we can call him Google or own Google. So, well, I to appreciate it. Yeah. Thank you guys. Great seeing you again. Thank you. Appreciate you. And the camera died right at the end. Oh, did. Yeah. Which is interesting because

Owen Audio (1:19:57)