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Fail Forward to Scale Faster: Vulnerability, Networking & Mastermind ROI for Real Estate Investors

By October 20, 2025Real Estate Pros Show

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Show Summary

In this conversation, Jaysum Hunter discusses the importance of advisory services and the strategies for effective delegation in a corporate environment. He emphasizes the need for advisors to focus on their strengths and delegate tasks that do not align with their expertise.

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    Investor Fuel Show Transcript:

    Jaysum (Jay) Hunter (00:00)
    I add one thing to your viewers when it comes to that? ⁓ That this the one area that, like I said, clients pays me. And I get paid more than most advisors. I have a corporate background or corporate training, but I also saw that the industry was to sell.

    Quentin (00:04)
    Absolutely.

    Jaysum (Jay) Hunter (00:27)
    Now, like they were trying to be like the Walmart and I’m like, no, I want to be the opposite. ⁓ But it’s delegate, outsource or delete. If that’s not your strength, you need to delegate it, you need to outsource it or you need to learn to delete it. And when the clients, like I said, that pays me, when they hear that and when they actually implement it,

    You know, they always come back to me and like, that was the best advice, you know, you gave me. And it was simple. It was nothing, you know, hey, let’s do some calculus. Let’s crunch up numbers. Let’s do some pro forma. You know, that was one of the, you know, but that’s a ⁓ easy win for most people business.

    Quentin (02:49)
    Welcome to the Real Estate Pros podcast. I am your host Q Edmonds. Excited to be here with you today. Wow. Looking forward to you guys hearing from my guests. We’ve been talking and I am, like I say, excited when I get to see things from somebody else’s unique lens, unique perspective, unique experience. And that’s what I’m excited about today. I’m excited.

    to introduce you guys to Mr. Jaysum Hunter. He said I can call him Jay. Listen, y’all can’t call him Jay just yet unless he give you permission. So I’m going to put some respect in him saying this is Mr. Jaysum Hunter. How are you feeling today,

    Jaysum (Jay) Hunter (03:31)
    Now I appreciate that Q and you know, I’m feeling blessed. I’m feeling not feeling as good as you with the pink shirt on, but you know, I am feeling well man. Like I said, I’m ready for the fall winter, fall and winter here in Chicago man. I’m ready to close more deals man. So I am ready to give more knowledge out there in this world because you know, there’s a lot of

    Quentin (03:38)
    You

    Jaysum (Jay) Hunter (04:00)
    know, fakers in this business. So I kind of want to just give them real. And I think a lot of people, when they hear the real, they hear the truth, you know, ⁓ the truth do something to them, you know.

    Quentin (04:02)
    Yeah, yeah, yeah, absolutely.

    Yeah,

    yeah. What they say, man, they say real recognize real. say the truth set us free, you know. And so, man, so, yeah, so I definitely I want to dive in. I you to take our viewers and our listeners, give them a short version of what it is that you are involved in these days and also tell them what market you’re operating in as well, brother.

    Jaysum (Jay) Hunter (04:19)
    Yes, yes, yes.

    Yes, you know, ⁓ I’m based out here in Chicago, you know, like I said, one of the greatest cities in ⁓ East America, but it’s also been, you know, I think, kindies, ⁓ you know, travelers, you know, named Chicago as the best city for eight years in a row now. And that was the best city in the world,

    you know. So I know we get a lot of negative media, but, you know, don’t always accept.

    which you see in the media, least mainstream media. So I’m here and I mostly focus and work with entrepreneurs, investors and founders that’s looking for a trusted advisor. My background is in finance and accounting and I do like a lot of founders and investors that I work with.

    They own real estate. They own some of the best real estate here in Chicago. ⁓ So if that’s a ⁓ 12 unit or just a multi-unit, it’s helping them understand the numbers, calculate performance. But they all are business owners. So I really, you know.

    focused on the business side with them and also the real estate side of them kind of connected together. And then I’m also for myself, you know, as an investor, I’m looking for a portfolio, you know, a company, a ⁓ real estate, but for me, I like business. So I don’t do just one off. I need to like purchase like a REIT, you know.

    a real estate trust, investment trust. So that’s kind of where my game is at. But the investors and the founders I help, if they’re a coffee shop and they got six to eight locations, they own their buildings. But we have to make it be profitable. We also gotta make sure that they understand the depreciation.

    Quentin (07:36)
    Hmm.

    Jaysum (Jay) Hunter (07:45)
    you know, how to write that off without trying to, you know, go into jail, you know. So, I basically helped them, you know, with that, you know, being just one phone call away, one email away, you know. Yeah, you know, and just trying to be vulnerable as much as I can, you know, I don’t know everything, you know, but try to give them the help and guidance, you know, when they need it.

    Quentin (08:11)
    Absolutely. Now, man, I love it. I love it. I love your consistency and your dedication to helping investors, helping people with their money. Like you said, helping people protect money the legal way. You know, I love it. I love it. And you and I, you know, we was talking. It’s not always especially easy in this climate. So what’s been the key to keeping that machine running smoothly?

    Jaysum (Jay) Hunter (08:27)
    Yes, yes, yes.

    Hmm. You know, something that we just talked about is being vulnerable, you know? You know, I share a little tough times for me, you know, a few years ago, you know, when the sky wasn’t, you know, looking so blue, you know, and I find like, you know what, I have to lean 100 % into the business.

    It was a business partner that let me crash on his couch. So I can focus on the business. So I can focus on growing and scaling. So small acts like that really has helped me continue when, like I said, maybe this guy was great.

    or you just didn’t know exactly, like you knew you had a big mission, but you didn’t know the next steps in the mission. So just kind of being vulnerable, but also always sharpen up your skills, always sharpen up, going back to that,

    I’m always reading, I’m always looking for new deals, not just for myself, but for clients and for others. So people…

    always contact me like, hey, what you working on? What you looking at? Like ⁓ I said, spent hundreds of thousands on ⁓ if that’s masterminds, if that’s being part of network groups, just being around smarter people or other experts.

    ⁓ that can help me level up. ⁓ And just standing in faith, being grounded in faith ⁓ has always helped, like I said, through adversity. ⁓ And one of my mentors who I never met, Warren Buffett, always says, the best investment is an investment in yourself. So.

    Quentin (11:35)
    Hmm.

    Jaysum (Jay) Hunter (11:36)
    I know that with that 100K, with the school and with all the investment in myself and into my business, that it has to continue to pay off. So why stop now? Keep going. So that’s kind of where my head is at when, like I said, disguise is not…

    you know, as bright as it is when you first get started. When you first get started, know, your eyes get big. You think you, you know, you’re going to do numbers, you know, quick. And sometimes it don’t work out that way at all. And sometimes you got to take a humble, you know, piece of that humble pie. And, you know, a few years ago when I had to, you know, move in with a business partner, that was my humble pie.

    Quentin (12:05)
    Yeah.

    Yeah. Man, thank you. Listen, thank you for the gift of your vulnerability. Actually, that’s something that we do here with this podcast. We always like to talk about, know, people talk about the success, but sometimes we don’t talk about the journey, the process to get into success. And so we always try to take time out here on this podcast to do that. And you just so naturally, so vulnerably went there. And man, I appreciate you for that because you’re not by yourself, you know.

    And I know you have probably on the other side of that obstacle, but of course, adversity is not new to just you and me, right? It’s so common to everybody. Actually, failure is part of success. How do you know how success look without failure? teaching your kids that failure is not a dirty word, you know what I’m saying? Like we can fail forward, right? The ultimate time.

    Jaysum (Jay) Hunter (13:19)
    Yes, yes.

    Yes.

    Quentin (13:25)
    is when we quit, right? When we decide that we don’t want to do it anymore. And that’s not what we’re talking about. We’re talking about pushing past moments that was just a momentary setback that was just setting us up for the comeback, right? And so, man, I thank you so much, man, for that gift of vulnerability. And I’m so glad, you’re on the other side of it. Yes, sir.

    Jaysum (Jay) Hunter (13:35)
    Correct. Correct, yeah.

    And I want to add to that.

    Yeah, I would like to add to it because like you said, it’s an opportunity to come back. What I realized in my stage of vulnerability, it made me better in relationships. Because now I can’t just hold things inside. I have to learn to communicate what was going on.

    And once you feel once, you’re like, man, you don’t want to feel that experience again. let me make sure that whatever it took to get me here, I don’t want to go through that again. ⁓ So it really made me a lot stronger in my professional and even personal relationships from a communication standpoint.

    and then also understanding others and their needs and their vulnerabilities. Like you said, not everyone’s going to share their vulnerabilities, but sometimes you have to be on a lookout for them, you so you can either share it with them too, you know, so, and that will make sure a trusted advisor, trusted relationship and people who’s going to continue to work with

    or what some people would say want to shop with you.

    Quentin (15:45)
    Yeah, yeah,

    yeah. No, I I couldn’t say that better myself or something about there’s a connectivity that happened neurologically when you just share your vulnerability. Like when you show people like, hey, you know, like, no, you’re not the only one. And you might even not, you may not say those words, but just sharing opens up that bridge to say, ⁓ man, like.

    Jaysum (Jay) Hunter (15:46)
    Yeah.

    Quentin (16:13)
    people be stuck in their head like, Derek, I’m not the only one going there. Like, nah. And so you’re absolutely right, man. And it’s such a big part of business as well. You know, you make that real connection and real relationship, the point of relating within business. It makes the conversation, it makes the deal, it makes the negotiation so much honest and so much authentic. Because we know why we here. Somebody’s selling, somebody’s buying. We know why we here. But…

    Jaysum (Jay) Hunter (16:18)
    Yes. Yeah.

    Quentin (16:41)
    It don’t mean we got to be Neanderthals and be like at each other’s neck. No, this is what we’re humans. Like this is the part of the transaction. And so I love you man for saying that. let me ask you this. Yeah, yeah. Yeah.

    Jaysum (Jay) Hunter (16:53)
    Let me add one more thing. Let me add

    one more thing to that. I think I heard a shark. I don’t know which shark said it, but they talked about they wouldn’t even invest in someone unless they had a failure or, you know, or a vulnerability moment. you know, think about.

    Quentin (17:09)
    Yeah,

    absolutely. I love it, Well, listen, man, you want the other side of it. know, things are looking good. So let me ask you, what are you most focused on or scaling next? What’s the next real goal for you?

    Jaysum (Jay) Hunter (17:23)
    Man, that’s a great question. So right now I spend in my marketing team. that’s kind of got me out of the weeds of the thing. So next is I actually was, I used to be in your chair. I used to do some YouTube and ⁓ try interviewing. But I like my…

    gusto But something wasn’t right ⁓ And I realized I didn’t have the team so So next is probably you know building a team, know expanding a market team around, you know video content so ⁓ But then other than that it’s really you know to

    expand my clients but also expand their thoughts and their projects. I’d have a handful of clients that I can work with forever versus trying to always on this New Hampshire wheel of trying to get 20 new clients a week or 20 new clients a month. And you don’t even know if you’re gonna like them or you respect them or anything like that.

    You know, so trying to get clients to like, man, this shouldn’t be your last project. You know, yeah, you know, it’s the climate is not the best at the moment, but you know, it, you know, it’ll change because so many people are, man, what’s going on right now is affects them. And then, you know, three months later when the skies is a lot better, they have a

    another perspective, I can go for this forever. So just kind of keeping people and keeping clients, just kind of focus on their mission or their why, it’s really, it’s my goal. It’s kind of where I come in and lead the most.

    Quentin (19:34)
    Yeah. No, I love it, man. You, you know, really the next point that I want to go to you, cause you started talking about building a team and you talk about, I love how you said you want to build clients that you can work with forever. And you know what saying? I love that. So I want to talk about relationships for a little bit. So when it comes to building relationships and growing your network, what’s made the biggest difference for you?

    Jaysum (Jay) Hunter (19:59)
    You know, doing those investments, investing in those masterminds, you know. I threw a big name out, investing in a program like Greg Cardone. I visited him a few times in Miami at his university or his headquarters. And just get training around

    or being trained around experts and what you want to do, you know, because for me it’s not like, hey, I’m trying to steal someone’s blueprint. Well, I want to do exactly what they do, but they had to build a bigger company than I am. So least let me go into those rooms and see what’s, you know, he’s saying or what he’s talking about and what other people are talking about. Because you know, others won’t, you know, with the like minds going to be there.

    So, you know, joining the Chicago Chambers of Commerce, know, shaking hands with, you know, like some of mayors and, ⁓ you know, the local politicians, you know, and, you know, other entrepreneurs that, you know, might be investors. But sometimes, a lot of times, they just need someone to listen to, you know, listen to their problems of the day. And so that really has been, ⁓ you know, my saving grace.

    Quentin (21:19)
    Yeah.

    Jaysum (Jay) Hunter (21:27)
    I try to, I think I try to treat, you know, the people that work for me fair, you know. ⁓ It’s not easy because I focus only on results. ⁓ So, ⁓ but I do try to treat them, you know, as fairly as I can. And, you know, always looking to expand, you know, ⁓ you know, and, you know, that’s kind of where I’m focused. I’m focused on it really what helps me the most is, you know, networking.

    And just make sure that, all right, you’re not just going out and having cocktails, but you actually out there networking. What about you? What did you see as one of the biggest ⁓ ways that you grew your business or you grew your podcast? Because I see you have a lot of followers.

    Quentin (22:04)
    Yeah. Yeah. yeah, yeah, yeah. No, absolutely. You say you network.

    Yeah,

    absolutely. Nah, man. Yeah, no, I think you hit the nail on the head, The networking peak to the linking up with people, like knowing your strength and knowing your weaknesses and hooking up with people who expand and can help you with your weaknesses. So like building an ecosystem, right? When you do your strengths well, don’t overextend yourself. Don’t try to be something that you’re not.

    Jaysum (Jay) Hunter (22:26)
    is this right after something we did?

    Quentin (22:49)
    but connected with somebody that can apply the missing link to what you did. So everything you said, like the networking, I love how you said, you know, make sure you’re actually networking and just not there for the pina colada, right? You know, the pina colada is great. You know, the virgin daiquiri is wonderful, but that’s actually make real connections. But the point how you said earlier, authentic connections, not where we feel like this is just transactional.

    Jaysum (Jay) Hunter (22:50)
    Okay.

    Yes, yes, yes, for sure.

    Excuse me.

    Quentin (23:18)
    I mean, we know what business entails, but just because it is business doesn’t mean we’re not human. Doesn’t mean we make real connections, right? So that’s been the thing, man, linking up with people. I don’t have to this by myself. I’m only one piece to the puzzle. So that’s what’s been important for me. And I hear the same thing with you. And I think that’s what we’re really trying to get with, tell our viewers, you don’t have to do it alone. partnerships, real collections, connections. That’s why this podcast exists. Everybody around real estate.

    Jaysum (Jay) Hunter (23:45)
    Yes.

    Quentin (23:46)
    people doing different things. got you with advising, with investments. We know, rather be renovations, like investors. Like we want everybody to sell things from their perspective. And so that’s what I appreciate about you today. Being vulnerable, bringing your fresh perspective to our audience. has definitely, definitely been refreshing, man. So I thank you so much, man. I really do.

    Jaysum (Jay) Hunter (24:10)
    I add one thing to your viewers when it comes to that? ⁓ That this the one area that, like I said, clients pays me. And I get paid more than most advisors. I have a corporate background or corporate training, but I also saw that the industry was to sell.

    Quentin (24:14)
    Absolutely.

    Jaysum (Jay) Hunter (24:37)
    Now, like they were trying to be like the Walmart and I’m like, no, I want to be the opposite. ⁓ But it’s delegate, outsource or delete. If that’s not your strength, you need to delegate it, you need to outsource it or you need to learn to delete it. And when the clients, like I said, that pays me, when they hear that and when they actually implement it,

    You know, they always come back to me and like, that was the best advice, you know, you gave me. And it was simple. It was nothing, you know, hey, let’s do some calculus. Let’s crunch up numbers. Let’s do some pro forma. You know, that was one of the, you know, but that’s a ⁓ easy win for most people business.

    Quentin (25:27)
    Yes, sir. Now you hit the nail on the head, you know, I often say, and I think it’s around the same exact thing, either delegate, automate, or eliminate. Like you got, I mean, getting your time is our most precious commodity. That’s the thing that we have that we try to leverage is our time. So whenever you can get your time back by delegating it, automating it, or eliminating it, you can get your time back one way or another.

    Jaysum (Jay) Hunter (25:38)
    Yes, yes, yes.

    Quentin (25:57)
    And that way you can see clearly on what you need to focus on to grow. So I love what you said, man. You said, you’re trying to be the opposite of Walmart. And I get it. This is, I get you, sir. I get your mindset for sure, man. For sure. So Jay, man, I appreciate you, brother. I appreciate you so much. Listen, before we wrap, if someone wanted to reach out to you, connect with you, maybe collaborate with you or learn more about what you’re doing, how can they reach out to you,

    Jaysum (Jay) Hunter (26:06)
    in the event of an accident.

    Okay. So Q, once again, thanks for having me on your podcast today. And, know, once again, if you guys have faced any of these challenges, you know, you have some bottlenecks in your real estate business or, you know, portfolio company business. If you’re looking for just working capital or, you know, being able to fund your next project, you can reach me at, you know, my business Instagram, 575ASM.

    That’s once again, 575ASM. We basically educate, you know, the next great finance and accountant professionals on that. But we also, you know, you have the opportunity to get working capital. You also can reach us at 575ASM.com. again, that was 575ASM.com. And if, you know, like I say, you want to work directly, 312-639-4050.

    again that’s 312-639-4050 and you know feel free to shoot me a text or give me a call directly and you know I might either EA or I will you know respond to you as soon as possible ⁓ but you know that’s it.

    Quentin (27:39)
    There you go. Listen, Mr. Jay Hunter, Jay sir, I appreciate you, man. Thank you so much for your time. Thank you for your story. Thank you for your perspective. We absolutely need people in this space doing it the right way. It’s just like you, man. So thank you so much.

    Jaysum (Jay) Hunter (27:41)
    Okay.

    Nice, I appreciate that.

    Quentin (27:54)
    Absolutely. So listen, y’all got him? Listen, y’all got the value, y’all heard Jay, y’all know we’re going to continue to spring up valuable people. And so please make sure you hit that subscribe button. That way when an alarm and alert goes off, you can just come and just enjoy the show. So again, thank you, Jay. And to everyone else, we will see you on the next time.

    Jaysum (Jay) Hunter (27:57)
    Yeah.

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