The Raising Capital Show · 2025-07-01 · 24 min
Nate Dodson, host of The Raising Capital Show, discusses the critical distinction between selling investors and traditional sales. Drawing on his background as a stockbroker in a high-pressure environment, he argues that successful investor relations depend on authentic relationship-building rather than aggressive closing techniques. The core insight: when asking someone for $100,000 or a significant percentage of their net worth, an emotional and trust-based connection must precede the ask. Dodson advocates for SPIN selling methodology - understanding prospects' current situations, problems, and future aspirations before presenting solutions. He emphasizes spending 50% of initial meetings getting to know prospects (their interests, experiences, background), 10% learning about their situation, and only 5% discussing the actual deal. Follow-up meetings should happen organically through activities like golf outings rather than marathon consultation calls. The Investor Attraction Academy and findmoreinvestors.com are positioned as resources for mastering this relationship-first approach. Dodson stresses that while webinars, AI automation, and drip campaigns have value, they cannot replace direct phone conversations and personal connection-building when substantial capital is at stake. He also discusses borrowing credibility from mentors (like his partner Jim) to establish authority without overselling.
Closing strategies like 'do you want $50k or $100k' work in transactional sales but create an 'icky' used-car-salesman feeling in investor relations. The relationship approach focuses on understanding prospects' problems and aspirations first; closing becomes secondary when trust and genuine connection exist, making aggressive closing tactics unnecessary.
Ask genuine, open-ended questions about their life, experiences, interests, and passions - the same way you'd naturally make a friend. Find one authentic detail (e.g., where they live) and let the conversation snowball naturally, gathering information while building rapport. This should take roughly half of an initial meeting.
A 20-minute call is never sufficient for a six-figure ask; it requires a series of phone calls, meetings, or activities like golf. Within each meeting, spend 10 minutes on rapport and discovery, 5 minutes explaining the deal, then open the floor for questions - but don't answer all questions in one call; schedule follow-ups instead.
Rather than answering exhaustively, acknowledge the questions, express genuine interest in addressing them fully, and suggest a follow-up meeting ('Are you available to play 18 holes next week?'). This respects their intellectual engagement and prevents the meeting from extending indefinitely, which signals low purchase intent.
Webinars, email sequences, and AI can pre-educate prospects about your asset class and criteria before meetings, keeping you top-of-mind, and automating routine communication. However, they cannot build the trust and emotional connection required for five-figure-plus investments - that demands direct phone calls and personal conversations.
Computed from the transcript - who did the talking, and the words that came up most.
In this episode, Nate and Jillian show us what it really takes to sell investment opportunities the right way. Spoiler: it's not about being pushy - it's about building real relationships. Nate shares why raising capital is different from selling anything else and why trust, connection, and good old-fashioned conversation matter more than slick pitches. From avoiding the hard close to leveraging credibility and using tech wisely, this episode is full of real-world tips on how to
Transcribed and scored by The B2B Podcast Index.
Speaker A: Hey, guys, thanks for joining today, the capital, uh, raising show. It's, uh, me, Nate Dodson. I'm, um, joined here with the amazing, lovely educationer, Jillian Sedoni. Is that even a word?
Speaker B: I don't know, but it's our new word, though. I'm edumacated.
Speaker A: I'm going to get you the little, uh, desk plaque that says edumacator.
Speaker B: Edumacated.
Speaker A: I love that.
Speaker B: All right, so, but I'm.
Speaker A: Today we're.
Speaker B: Today you're going to educate.
Speaker A: Today I'm here for that. I'm, um, we're actually talking about one of the things that I'm most passionate about, which is actually the sales, selling investments to investors and just kind of how that works. So I, I appreciate everybody that's joining today. We're going to get a little bit more into it. I hate to say and admit, and we're going to miss you, Jillian, that you're probably gonna have to jump a little bit early. Doesn't matter. I, I like to hear myself. So I'll just keep on, gonna keep
Speaker B: on going, keep on rolling. All, uh, right. All right, well, listen, I am excited because you're going to be talking about sales, and I feel like I'm very, I'm like, okay. At sales. So I'm very excited to hear what you have to say about selling because I know, like, you almost study it. You almost like, like read every sales book out there.
Speaker A: No, no, literally read every sales book.
Speaker B: Yeah. No, and the, the thing I, I noticed, like, uh, you guys have to know this about Nate is we'll be in conversations with people and he'll like, after the conversation's over, to me privately, will identify the sales process the person used. Like, that's how good Nate is. So you gotta lean in today because he's gonna give you some like, really kind of ninja type techniques on, on selling and specifically selling when it comes
Speaker A: to raising capital, which honestly is a little bit different than, than the norm. It's just kind of positioning wise. But more than that, uh, I'll be just frank. When you're asking somebody for $100,000, it's way different than selling an office printer, at least.
Speaker B: And thanks for sure you're going to get something from the printer.
Speaker A: I mean, it literally is even working with people within our investor attraction academy and what they're interested in. It's far different than, you know, I have crowdfunding lawyers, but then meeting with somebody there, if you need a lawyer, you know, you need a lawyer. So that's the way that I'm going to talk to you. But then with Investor Attraction Academy. Ah man. We're just here to help you find investors in ways with strategies that really nobody else is using. I love having those conversations because it's exciting for me too because we're actually providing something of value and that's important to convey. That's just kind of part of the, it's the sales process, but it's also a passion.
Speaker B: Okay, so can you back up for a second? Let's talk about there. There's, there's the sale, but then there's the process. What, what do people have to be think when they're thinking about their sales process?
Speaker A: Yeah, I mean it really starts with you're asking for a lot. Sometimes it's a huge percentage of net worth. No, I mean that because it's emotional decision for a lot of people.
Speaker B: Oh, uh, sure. Absolutely.
Speaker A: A technical decision for the engineers of the world. And going into it, you don't really know what kind of a person they are. So the most important thing at first is to get to know people, become friends.
Speaker B: Oh, so you're suggesting part of the sales process would be to get to know your investor before you even get them to invest. Like in other words, don't rely on the kindness of strangers.
Speaker A: You know, one of the worst things if you're trying to sell an investor. And I, I do know a lot of these guys that are successful doing it. Is that hard close. Sounding like a car salesman like that. It's just that icky feeling. Before I was ever an attorney, before I was doing any of this stuff, I was actually a stockbroker banging on the phone with basically a boiler room listening to people that were successfully selling all day. And there were so many used car salesmen in that room. But the guys that really made it far superior took the time to get to know who they're working with to build the trust. Mhm. So that, that's definitely step one. And if you're thinking this is a one call close, you think you can just have a 20 minute phone call and then give me the money because I'm buying this apartment and you need to move now. There's not a lot of success there.
Speaker B: No, no, no, no. But tell me about that. Let's talk about that because I think that's very interesting about, you know, the stockbroker who got people to invest more money because they got to know the client. How do you, how do you do that without sounding like a creep? Like, tell me all about you. Tell Me about your children. When's your birthday? How do you, how do you get that, that, that vibe going?
Speaker A: How do you make a friend? We've all done it. I mean, it's, uh, it's now we're, you know, not spring chickens anymore. We're not in school. We're not constantly surrounded by new people.
Speaker B: Right? Right.
Speaker A: You know how to make a friend.
Speaker B: Right?
Speaker A: Right. And everybody you work with should be your friend. And you should be genuinely interested in what's their dog's name, what are their passions, what are their interests, what's their experience? Because their experience builds who they are. So you don't need to be awkward about asking. But Jillian, I know that you live somewhere that is really so remote and amazing and tropical. Can you share a little bit more about kind of what your day to day looks like? Because I'm interested.
Speaker B: So. Okay, that's interesting. Because that's interesting.
Speaker A: No, no, no. Um, I'm really interested. Uh, what's the day to day like? I'm asking you a question here. Tell us about Puerto Rico.
Speaker B: Well, I live on an island. Um, I live two and a half hours away from the major city. So, um, I'm in a town of 13,000 people. But I'm looking at the ocean right now, which I wouldn't be able to do if I continued to live in Southern California. And I go to the beach every single day and walk with my dog. And that's what makes it amazing. So if I want to get back to the rat race, I can just take a two hour plane to Florida.
Speaker A: It sounds like you've got an amazing life. You must have been successful in the past. What kind of, uh, like what got you here? Like, how are you so lucky, hard working, how are you so amazing to get where you're at, Yada, yada, yada.
Speaker B: You're good. No, but that's good because that's information that's easy to come by. Right. You, like, already know before you get on the phone with them that I would be in Puerto Rico. Like you would have that information. So there's some. It sounds like to me, you can correct me if I'm wrong based on what you just did, is that you just have to find where you can peel the sticker back from. Like, where is it lifted just a little bit, that I can peel it back a little bit. And you, you found that one thing. Like, I live in Puerto Rico, so that will snowball.
Speaker A: And now I'm asking about what you've done. Um, next I'm Going to be asking, oh my God, you had this job, but man, you've got an amazing life. It sounds like you've been very successful investing as well. What's, what's been your strategy? So it's like you can have this very natural get to know you conversation, but you're still just gathering data all
Speaker B: along the way, you know, and actually that like I'm losing money on a, on a. I've had like a lot of people have had a couple of deals go sideways on me in the last several months actually. And if you, if you had said something like that to me, that would be almost like a great opportunity to build some trust on finding out why my deals didn't work, what went wrong, why I shouldn't have done that deal, and then differentiating yourself from those deals that I did. There.
Speaker A: There's a concept called spin selling that uh, it's, it's how to sell without actually closing. And it is all about getting to know people, authentically understanding their problems, understanding where they're wanting to be. What does your future look like? And what I'm hearing you talk about are problems. And you have to either solve that problem or overcome that problem. And thankfully, I'm truly here to help you do that. I want to help you do that. I've got the only few ways that I can, and I don't want to be pushy about it, but I want to dive in a little bit deeper just so that I understand whenever it is time to ask for the money.
Speaker B: So. Okay, uh, can we back up for a second? Because you said some really interesting things there. Spin selling without closing. But you do have an ask, is that right? Like, so explain the difference to me before asking and, and, and closing.
Speaker A: There are closing strategies and these are things like, so do you want me to put you down for fifty thousand or a hundred thousand? The alternative, close. Mhm. And there's a whole bunch if you want to learn how to close and you want to learn how to use that. Kind of like, who is it? Ziglar. Zig. Ziglar. Tracy. Brian. Brian. I don't know.
Speaker B: Brian. Tracy, I know who you're talking about. Yeah.
Speaker A: But they've got some amazing books on closings and closing strategies and it's important to know and understand those. But that's also some things to avoid. At the same time, if somebody sees the benefits of really what you're talking about, if they know you because of how you've gotten to be friends, then they like you. Throughout this process, you should Be sprinkling in those. This is what I'm doing. This is how it's been working. This is why it's been great, you know? And honestly, like, I didn't really know much about commercial real estate until I started working with Jim, who has done it 500 times, has had so much success. And so now I'm doing these deals with Jim, borrowing people's credibility and their authority.
Speaker B: M. Oh, that's interesting. But can, can we talk about something else? Like something that I struggled with when I was doing sales for my business. Of course I think I still struggle with, is that you're talking about getting to know somebody and spending time with them and becoming their friend. I get that. But it's too much. Too much. And like, I used to notice that if I spent, I do 20 minute consultations, right. And then if I went like 15 minutes over that consultation, I knew I wasn't closing them. Like, it was almost like I'd given them too much, you know what I'm saying? So where is that line? And, and another thing is too, like, I have a mastermind with a different company and I can honestly say, like, my oldest friends aren't in that mastermind. Why, why wouldn't they want to sign up for that? I think it's almost like they don't, they don't understand why they'd have to give me money. Right. She's doing. Am I making sense right now? Like, what I'm saying, it's like, so I'm wondering where that, where do you draw that line? When do you go too far? When do you make it so that now you've created this relationship where they don't want to invest because they know you too well or something like that.
Speaker A: Let me use your 20 minute consultation as an example.
Speaker B: Okay.
Speaker A: And let me speak to it. Kind of like if you are asking for 50,000 or $100,000, you're never going to accomplish that in 20 minutes. It will be a series of phone calls or meetings or go play golf. But there is, in this example, I would probably spend 10 minutes half the time learning more about them, sharing some stuff about myself, sharing some stuff about the company. But not like, uh, this is what it is. But like, yeah, no, this has been our experience and how it's been great. I want to speak less than the prospect. They need to be speaking a majority of the time. And the less I can say, but still communicate authority, Communicate that experience. Uh-huh. That is necessary as well. But I'm spending half of that time Getting to know people. My actual explanation of the deal, what we do, what's our service? Five minutes at most.
Speaker B: Okay.
Speaker A: I uh, just that that should be the smallest part of this consultation. And then people have questions. Now they're finally comfortable to answer it because now they like you, they trust you, they've gotten to know you, now you've gone through. Here's really what it looks like. So let me open the floor. What questions do you have? I want to be responsive to you.
Speaker B: Okay, so, so maybe it's a little different because I was selling like a service as opposed to an investment opportunity. When do you cut the questions off? Because that's always where I'd get tripped off. Like we talk for 20 minutes, I get to know their business, I tell them the basic information that they needed and then the next 15 minutes were me answering their questions and I just knew, I knew like I'm never going to close you.
Speaker A: And a lot of those questions.
Speaker B: Ah.
Speaker A: And now let's, you know, speak. As an attorney. Mhm. A lot of those questions. It's not appropriate for me to answer today or it's going to take so much longer to explain that. And I don't have the time as an attorney. We don't have that relationship, that uh, attorney client relationship. Well, if you're selling an investment, like I'm not even going to pitch you on that first phone call because it's inappropriate for me to pitch that at that point. But you know what I am going to do? I'm going to respond to it in such a way that's going to encourage a follow up communication, a follow up discussion. I just don't have the time to go that deep with you. But I really want to answer your question, I really do. You available for uh, to play 18 holes? That's next week.
Speaker B: Ah, so what, uh, that's good. Oh, so maybe that's exactly what you can do with an investor then is like, listen, I understand you got a lot of questions and I want to answer all your questions. Are you available to play 18 holes next week instead of continuing that conversation right then and there or should you just continue until they've exhausted all their questions? And I'm actually just uh, so you know where I'm coming from. I'm actually thinking of an investor right now who invested with couple of people I know. And we all wish she never invested. Right? And I think about her and I think about all uh, right. I wish she never invested. And my first clue should have been the amount of questions she Was asking, is there a time where somebody who, you know, I want to be respectful to these syndicators and these fund managers. Right, These fund managers, their time is precious. So yeah, so I'm thinking about our audience right now who's listening to this and going like, I don't have time to answer all these questions. How can they mitigate that by technology? Okay.
Speaker A: One of the best things to do is to create that funnel that you go from that initial contact and then have a webinar, have a way that they can spend 10, 15 minutes getting to know the. You getting to know your business, getting to know what your asset class is, why you like it, what criteria are you looking for? And you give these people this information before you have that first discussion. And then kind of part of the secret. And I'm just going to bring this up if you want to understand and learn more about the secret sauce of really how to make this work. Personally, my partner Jillian, love to work with you at the Investor Attraction Academy. Just check us out. You can go ahead and get started at, uh, findmoreinvestors.com there's the pitch. But you know what, I just want to mention it and then let's move on. But that is really what's going on. And you know what, There should always be some sort of a follow up, nurturing communication sequence that goes on during time. But it's not just you making phone calls. It's not just you sending them a webinar that provides some ongoing reminder of staying top of mind, providing value through the communication. But what you can never do through that drip process is get to know you. Um, that can only happen by having that conversation. We talk about the wonderfulness of AI. And I know more and more people are really doing outreach and marketing through AI. Maybe I'm old fashioned, I've said it before, I'll say it again, techno caveman. I would rather pick up the phone and get to know somebody and talk to them any day of the week, because that's how I get to know them. But you know what, I'm going to send a webinar, I'm going to point somebody to our YouTube.com/entrepreneur. It, uh, looks like we just lost Jillian. But when I talk about this sales process and I'm literally doing a class where we have modules so that you learn the process that I'm talking about right now so you understand how to approach an investor, to lead them through a journey to get to know you. But where I was, uh, really ending up before Jillian went ahead and, uh, jumped right there or got lost. I mean, Puerto Rico. She probably loses Internet for hours or days. AI is great to automate things, but AI will never build that connection that you need to have. When you're asking for a hundred thousand dollars, when you're asking for a large percentage of anyone's net worth, there is no replacement for you to communicate with people online through direct messaging, through email, that you actually write, through the phone calls that you actually have, where you're building the relationship before you ask for the money. And I've said it before, I'll, uh, say it again. I'll say it repeatedly. The closing strategies are important to know, but it becomes less important when people understand where they're at, where they're trying to be, understand how your opportunity can help them bridge that gap, and then they have that trust in you again. You're never going to do this with an email that is not from you. You're never going to do this from a webinar. You're never going to do that through AI. They have to trust you to be that right person with the right business. And when I talked about Jim, the mentor that has the opportunities OR has closed 500 deals in the past, your prospect is trusting you because of your association, mentorship, and working with Jim, that's how you're borrowing people's knowledge, you're borrowing their authority, you're borrowing their track record, so that at the end of the day, you still come out looking like a champ. We are barely scratching the surface about how to really make things successful. And we haven't even touched on, nor can we in our short few minutes. I know you have questions, you should have questions, and I'd love to answer those, but it's going to be talking to you and getting to know you. So my big point is, thank you so much for joining today. And just to throw it out there, if you want to learn more, check us out@, uh, findmoreinvestors.com and I would love to actually meet every last one of you. I talk about passion, and this is a huge part of my passion, is getting to know people that are in the same industry, that are doing the same things, that have the same interests. And, uh, my interest is helping you find more investors, sell more investors, reach your goals. Because at the end of the day, if you do better, we do better, and everybody wins. Long story short, for a short time, again, reach out anytime, and I'm looking forward to it. So we dived in a little bit into what it looks like to sell an investor. We're scratching the surface. There is so much more to it and I'd love to share it with you. That's what we're doing to help our members. That's what I'd love to do to help you. But thank you for joining all day today. If you actually made it this far in it, I wish I had one of those like let me give you something nice so I don't just reach out at any time. Uh, but until then, I hope you have an amazing time getting to know people, that you're getting more deals done and your good old fashioned pick up the phone and reach someone. But thanks for joining for the capital raising show, I'm Nate Dodson and we had a Jillian around and, uh, now the Puerto Rico has swallowed her up. But we'll see you next time. Thank you all. Talk soon.
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