The 5 Questions Podcast
Join us as we unlock real estate and business insights, one question at a time.
The 5 Questions Podcast
Why Real Estate Is More Than Money: Building Legacy, Teams & Impact with Diana Khan
In this episode, we explore how a home becomes the center of value — not just an asset — and why the most impactful investors build businesses around life transitions, community, and legacy.
We unpack how to structure deals that solve real problems, strengthen your team, and grow through discomfort and trust. Whether you’re a new or seasoned investor, these insights will reshape how you see opportunity, risk, and relationships in real estate.
What you’ll learn:
- Reframing real estate as legacy, community, and daily life
- Structuring LOIs with non-price levers to create win-wins
- Building a reliable team to reduce surprises from offer to close
- Why saying “yes” before you’re ready accelerates growth
- How conversations—not assumptions—resolve conflict
- The 3 non-negotiables for scaling: work on it, cash buffer, 60-day yes
- Why your first hire unlocks capacity, systems, and peace of mind
Connect with Diana:
https://www.dklawmd.com/
Saying yes to something before you're ready is what you need to do to grow.
SPEAKER_00:Welcome to the Five Questions Podcast, where we unlock real estate and business insights one question at a time. Welcome to the Five Questions Podcast. My name is Mario. I am your host, and our guest on today's show is an attorney, a real estate broker, a multipreneur behind seven driving uh companies, founder of DK Law Group and nationally requested keynote speaker. I welcome Diana Kahn. Deanna, welcome to the Five Questions Podcast today.
SPEAKER_01:Thank you for having me. I'm so excited to be here. Anytime I get to be on a podcast, especially one I listen to, I get so excited.
SPEAKER_00:Well, thank you. Uh Diana, the uh concept of the podcast, real simple. I ask five questions either about real estate or business, and we get straight to the point. You ready?
SPEAKER_01:I love it. I'm ready. Let's go.
unknown:Okay.
SPEAKER_01:Let me take my pen. I'm gonna take notes while we talk. Go ahead.
SPEAKER_00:You've built seven companies across law, brokerage, and title. Uh what was the inflection uh inflection point that moved you from practicing attorney to multipreneur? Uh and what principle still anchors every decision you make today?
SPEAKER_01:So I think, you know, I was originally in real estate before I went to law school. So I had my real estate brokerage first. I sold houses. And then when I went to law school, I said, I'm never doing real estate again. Like it's never doing it again. And I think a lot of people in real estate say that. But when I got out of law school, I realized that really one of the things that's most magical, at least in the United States, I'm not originally from here, is that our homes are not just places we live. It's where we do everything, right? It's our biggest enterprise, it's our biggest investment. It's really it, at least in the American nation, it's also kind of what we die with, right? It's it's kind of where everything is done. It's not just a place you sleep at night, it's where your kids kind of take their first step. And when I started realizing how much we actually equate happiness and legacy, well, there's got to be a way to incorporate that within everything I do. So, you know, I kind of went with this idea of a house is not just a home, it's what you make of it. And then from there, I started doing all these businesses that are really centered on helping individuals not just sell and buy homes, but downsize a home, help grandmothers, help, you know, help your mom. And when you kind of see it as this centerpiece to everything we do in our lives, and that's why most of people's whys break down to what they do at home. And then from there, my company's kind of branched out, and it's just been it's been fun ever since.
SPEAKER_00:So the the way, yeah, so basically you don't take um your decisions on what I would call the moment, but uh make them more on the big picture. Uh like you say, this is not where I just sleep at night, this is my home. And what is included in my home is is experiences, it's memories, it's everyday life uh stories. So I I like that.
SPEAKER_01:And it's it's also the idea, really, is when you where you live is also socioeconomically where you shop, it's where you put into your community, it's where you want to help your community. So when you build businesses to kind of mimic that community, it can really kind of speak to terms. And then when you have seven businesses across the scope, then you can help somebody with their home in different ways, be able to feed your own kids, but not necessarily be looking at the bottom dollar as a transactional that just occurs one time.
SPEAKER_00:Yeah, I I I agree with you. Um second question I got for you, and this has to go with real estate investors and and maybe law at the same time. Since you do both, I'm gonna ask you this for uh founders or real estate investors. What is the, I would call it number one legal blind spot you see uh at the LOI or the contract stage and the simple process you recommend to prevent it from killing the deals?
SPEAKER_01:I think investors a lot of the time look at them as deals, right? So when you don't like you get that letter of intent, you're putting it out, you make a mistake of thinking everybody's bottom dollar is just money. But really, I think a lot of investors that I work with become more seasoned or they become more experienced when they realize sometimes you can offer a seller$10,000 less, but offer them a moving company and an ability to downside. Or, you know, I'll help you get in your new home and kind of build this ability to kind of have candycap accessibility. And when I kind of broke away from just look looking at a letter of intent of just what is their bottom, and I want to get to that bottom and I want to make sure it's profitable for me, I actually became more profitable when I found out why they were selling and figuring out how I could structure a deal that's outside of those four corners of a contract, which is counterintuitive because lawyers always say the contract is just the four corners. But if you get outside of those four corners, you can get much further.
SPEAKER_00:Yeah. And then when you ask the right questions when it comes to real estate, for example, of why they're selling, I believe in win-win situations. So you can create a win-win outcome for not only you, but for the seller as well. And and then your name gets out there and you get referrals and you get more business. So I like that approach.
SPEAKER_01:Yeah, exactly. It's just, you know, kind of looking at it at a vertically integrated system and getting outside of the traditional norm that we're used to.
SPEAKER_00:Yeah. Question number three I have for you is you're a licensed attorney, uh, a certified mediator real estate broker, uh, you produce titles and a notary. I want to talk right now for small investors that are maybe starting. How should they assemble their deal to go from offer to closing with the fewer surprises as possible?
SPEAKER_01:Have a team and use them every time. I mean, I cannot say this enough. If you don't trust your team, that's a big issue. I think that a lot of investors, at least in the beginning, right? You're you're breaking every dollar, you're trying to make it all work. You won't go with the contractor that's a little more expensive. For me, I'm making more money when I'm not worried about money. So my team, even if they charge me a little bit more, I know they're gonna take care of everything. I know they're gonna flip that house, they're gonna do everything I need to do, and I'm not gonna be bothered unless the situation happens. That's not because they're the cheapest in the business, but I've built a relationship where it's people that will take care of those surprises for me so that I'm not blindsided when they happen.
SPEAKER_00:I I agree with you. I couldn't agree more because every time I took decisions in my past that I was trying to penny pinch or save. I I still remember a deal I did uh when I first started. I was trying to save uh and I was uh I was impatient and I had gone through many deals and it didn't follow through. I was dropping the deals, and this one I became impatient. I skipped on the inspection, trusting trusting the realtor because he knew apparently this deal. That mistake led me to lose$35,000 on that on that deal. Wow. So I cannot agree more than than what you just said is don't uh try to penny pinch or save some money on on stuff that you shouldn't save on. Right. Too many people try to you know to save a dollar in the wrong areas, it's gonna end up costing more.
SPEAKER_01:And and here's the thing, I don't believe anybody's in this world trying to take one over on you, right? I don't think I like to think that people aren't innately selfish, but I think sometimes there's a trust that's built in there. And perhaps what you value in a transaction is very different than me. But if we work together long enough, I'll know what's important to Mario, you'll know what's important to Diana. And that's that trust that you build and that learning skill set that works really well when you have a team that understands what your values are.
SPEAKER_00:Yeah, absolutely. Let's go to the fourth question. Um, your story centered on resilience, uh turning discomfort into growth. Can you share a moment where a major setback forced you to pivot? And what we want to know more is what did you change in strategy or systems or team that unlocked that next level?
SPEAKER_01:So this is kind of a weird one for me because I used to be the transaction coordinator. I was always in the back. I was, you know, doing things for other people. I was getting the contracts done. I didn't really like to be in the spotlight. It just wasn't for me. And then I just remember probably a few years ago, right when the interest rates started kind of going back up again. About three years ago, it was like Christmas, and I was at a Christmas party with all these realtors who were all top performing, we're all doing well. And my bank account was at like zero dollars. And I was like, this is not good. This doesn't feel good. And we're all pretending we're doing great. And I kind of realized that I've always kind of pivoted myself on helping others to a degree that I wasn't putting myself on the forefront because I don't feel comfortable, you know, doing a podcast. I don't feel comfortable being on TV. I don't feel comfortable kind of guiding that. So I kind of pivoted into that discomfort. And the next day I spent$15,000 on marketing for the following year. It was, I think, November, December. I never spent that much money on like backing my own name. But, you know, I was like, if I'm if I'm gonna go out broke, I might as well really go out broke and just completely downfall it. Put it all in credit cards, and I was so uncomfortable. I remember the first time I went on TV with like a commercial, I was like, God, that's gonna be that's not for me, right? And then my commercial went viral and people were making fun of it, and I just I just had to pivot into it. And now I just say yes more than I say no, but it's the discomfort of doing things and also I think finding out why you're uncomfortable with something because you and I both can not like public speaking, for example. But maybe for me, public speaking is about, I don't know, an accent. And for you, it could be about, you know, not liking your body or not feeling confident. You know, it's two very different things. So if you just say, I'm not comfortable with X and you don't know what X is causing you to be uncomfortable about, then you don't really get to know yourself. And that's kind of a deeper dive into it.
SPEAKER_00:Yeah, I I love that. And and you know, it comes down, yes, real resilience. Uh when you have failures, do you get back up and continue your journey? Uh, you talked about going all out. If you're gonna, if you're gonna fail, you're gonna fail for real. And right, and and and sometimes and if you look at you know, entrepreneurs that succeeded and now are millionaires and billionaires, they were faced with those situations. Right. Sometimes you have to take a chance in life on yourself. Do you believe in yourself enough and in your project or whatever you're working on to see it succeed? Do you do you know, do you feel it, do you visualize it? If you do, take the chance on yourself.
SPEAKER_01:100%. I couldn't agree more. And you know, the the thing I think that goes with that is you have to remember everybody else is trying to take chances too. I had this um just just this week, actually last Friday, this attorney was very unkind to me in an email. And, you know, I psyched myself out. Like, you know, it's not she had a bad day. I was like, she thinks I'm I'm stupid. You know, so she comes into the office the next day, and I mean it was a very bad confrontation. She comes in with her client and she sits across from me and I'm deposing her client and she's objecting and just being really strong. And I remember being intimidated by her. And then a little bit later, when when the deposition was over, I actually called her and I said, Hey, things got a little bad. Like, you know, let me tell you a little bit about me. And by the time we finished the phone call, ends up she was just having a bad day the night before. But what was very important is she told me that she had no idea what she was doing during the deposition. She was she was covering for somebody, she had very little knowledge about the case. Meanwhile, she was intimidating me. And she was like, I just didn't want to look like an idiot. And I was like, Well, that teaches you that we're all sort of sitting there doing the best we can, and we think other people have it more figured out and they don't.
SPEAKER_00:Yeah, absolutely. You never know. Asking, asking questions, and I liked what you did is you actually reached out to see what was going on. A lot of people won't, right? They're gonna either shove it under the carpet or they're gonna ignore it totally when sometimes it's a lot smaller than we think. Just have a conversation with the person, just try to figure out where they're coming from, right? Right. And that's what's missing communication a lot in these days, uh, these days in age, uh, I think would make a big difference on outcomes that people would have if they would take the time to have those conversations.
SPEAKER_01:And I think, you know, I think that's a little bit to be said about the way we text, right? Is like people have more conversations, but they're more scripted now. I don't think you catch people where it's like I'm just having a bad day. If you're having a text message conversation, it's not really a genuine thought. Like if you if I had texted her and I said, Hey, what was up with the email last night? She has time to react. She has time to kind of put the best face forward. Whereas if you just ask in a human way with like, hey, like you don't know me, but are you okay? Like, what happened last night? And that it kind of throws people off, but they get very appreciative, I think.
SPEAKER_00:Yeah. Deanna, uh, last question that we have for you today. Uh, you do you have many different uh companies? If a listener wants to scale from one venture into a diverse portfolio, okay, whether it's uh companies or ventures, what are your three non-negotiable um, for example, capital uh discipline, governance, people, process, whatever the case is, what are your three non-negotiable and what's one action that you suggest them to take in the next 24 hours to start uh scaling that that that portfolio or venture?
SPEAKER_01:That's a great question. For me, three non-negotiables is that if you're working in the business, you're not working on the business. And if you're starting a business, you need to be working in it enough to have staff. And sometimes people are like, when I get bigger, I'll hire people. But if you're working in it, you're not working on it. So you gotta do, you gotta get yourself to a point where you're always working on your business. And if that means, you know, nighttime after your business is closed and your clients are no longer available, that's the one thing is always work on it, not in it. If you have to do it, do it in both. I think a second non-negotiable for me is always have three months of expenses put away for just in case, for whatever you need and whatever that may mean. And if you don't have that, cut down your spending because you should be able to do three months if something happens to you right now. Be able to take care of the people around you, be able to take care of your family, whatever else may be. And then I think the third one is just say yes. You know, do everything you can for at least 60 days. Don't just say yes for a day, like put yourself to the test to something, fully commit for 60 days and then kind of see where it plays from there. Um, so I think that last one goes into what would I do tomorrow? Right. For me, I do everything I can for 90 days. And I remember the first time I hired an employee. I didn't listen to my own advice. I was working in the business to a degree that I was breaking down. I mean, it was I was too busy. I was too busy. I didn't have time for my kids. And I got this letter from my kids' school, and I have three young kids, like very young, and they were doing um costume day, costume day once a week once a day for five straight days. And 15 costume, you want me to buy 15 costumes for the following week with my business. And I just remember, I was like, I I can. So that day I text out a bunch of people. I ended up hiring somebody at$15 an hour, and she started the next morning. And I was like, I can't believe I just hired somebody I don't know. And I was like, I can't afford this. And then I was like, no, like I need it. And it was so crazy for me because I was like, I'm gonna be responsible for somebody else's pay. I'm gonna be doing all these things. And a year later I had over 70 employees, but saying yes to that first one and taking that bond was the biggest. And it took just kind of breaking down and realizing that like I need help. So sometimes saying yes to something before you're ready is what you need to do to grow.
SPEAKER_00:I agree with you. Uh yes, it the yes word is so powerful because it's the only word that opens doors. Yeah, you keep saying no, nothing's gonna change. Exactly. If it's the situation that you're in, if it's your finances, if it's your deals in real estate, if you say no, guess what? Nothing happens. But if you say yes, the door opens. Now, whether you decide to go ahead and go through that door, that's a decision you have to make. But the door is open. Right.
SPEAKER_01:So my dad used to say this joke when I was little. Um, and I never understood it because he used to say this guy, you know, he would pray to God all the time, and he would say things like, Oh, you know, make me a millionaire, make me a millionaire. And then years later he dies and he goes up to whoever he believes in and says, I pray to you every day to make me a millionaire, and you never did. And, you know, God or whatever it is that you believe in in that story responded back with, you didn't even go out and buy one lottery ticket. Like, how am I gonna make you a millionaire if you didn't take that step? Yeah, and it's a joke my dad shared with me when I was little, and I always thought about it, but it's true. You know, you can pray or you can believe or you can work hard, but you really got to take that additional step. And that step is founded in discomfort.
unknown:Yeah.
SPEAKER_00:Thank you so much for having the conversations uh with uh with me today on the the podcast. Very uh not knowledgeable. I can't am I gonna say that? I can't say the word, knowledgeable. Uh talking about accents before. And um I I really appreciate it. I hope our listeners will take a piece of your knowledge, your advice, and take it on their journey uh with them. I really appreciated our conversation.
SPEAKER_01:Thank you for having me. I had a great time.
SPEAKER_00:All right, we'll talk soon. Bye, guys. Thanks for tuning in to the Five Questions Podcast. If you enjoyed today's episode, don't forget to subscribe, like, and hit the notification bell on our YouTube channel so you never miss an episode. Stay tuned for more insights and tips to transform your real estate and business game. See you next time.