No Broke Months For Salespeople - The Secret to Real Estate Success Most Investors Learn Too Late | Nathan Payne

Episode Date: July 12, 2026

What You'll Learn in This Episode Why success usually takes 10 times more effort than you expect. The biggest mistakes new real estate investors make. How mentorship dramatically shortens your learning curve. Why blind optimism can either fuel or sabotage success. The importance of asking better questions—not just finding answers. How AI tools like ChatGPT can reveal your business blind spots. The difference between building wealth and designing a fulfilling life. Why consistency beats talent in entrepreneurship. Lessons from wholesaling that apply to every business. How to stay motivated when progress feels slow.     👉 Don't miss out! Sign up here:https://link.cpi-crm.com/widget/form/bJZ4NbRp6ZpSVgGoNb4j?notrack=true https://link.cpi-crm.com/widget/form/bJZ4NbRp6ZpSVgGoNb4j?notrack=true https://link.cpi-crm.com/widget/form/bJZ4NbRp6ZpSVgGoNb4j?notrack=true Shadow Hour Updates Stay informed with the latest updates and reminders for our Shadow Hour sessions. To find out more about Dan Rochon and the CPI Community, you can check these links:GET THE BOOK! Teach to Sell : Teach to Sell: Why Top Performers Never Sell – And What They Do InsteadWebsite: No Broke MonthsPodcast: No Broke Months for Salespeople PodcastInstagram: @donrochonxFacebook Page: https://www.facebook.com/NoBrokeMonths/Facebook: Dan RochonLinkedIn: Dan Rochon

You're listening to No Broke Months for Salespeople podcast. Welcome to the No Broke Months podcast. My name is Dan Roshan. I hope salespeople, entrepreneurs and business people have consistent, predictable income through the teach-to-sell methodology and technology. Today I am joined with Nathan Payne, who is a real estate investor. He's a consultant with years of experience structuring and negotiating off-market deals. He's known for his practical, no-hype approach to wholesaling that prioritizes transparency, strong buyer relationships and long-term success. What we're going to talk about is the secret to sales.

Welcome, Nathan. Hey, I appreciate you having me on here. I'm looking forward to our chat. So I am as well. So you are a real estate investor. Somebody that you, you know, you got started in wholesaling and investing and tell us a little bit about who is Nathan. Walk us through the cliff nose journey of what got you involved in this and interested in, you know, for this. We can go from there. Sounds good. Yeah. My name's Nathan Payne. I currently live in Canada right now outside of Toronto. I'm from the States. I moved here about a year and a half ago, but, you know, I'm just a family guy. I put family and God above all. You know, I think that's what life's about is, you know, putting others first.

And I've just gotten to real estate because I wanted to create my own path. I wanted to be my own boss. I realized the other day, I haven't had a normal, like, paying job in the sense of like working 9 to 5 or hourly pay. job since high school. I've been kind of doing my own thing since since high school. So, but yeah, I've just just a normal guy, nothing crazy about me. I've probably done some things that are crazy, but you know. One of the things that I, I tell others is that I've been unemployed for 20 years. Don't use that. You're married, right, Nathan? Yeah, married, yeah. All right. So for the, for the audience, the single members of the audience, don't use that on your dating profile. It doesn't work. No. You know. Entrepreneur, but you see, I.

see most people are putting that on their like profiles like whether they're an entrepreneur or not right. I'm just put it unemployed. I mean like I'm just putting I'm unemployable. That's yeah. Yeah. There you go. I like that. I like that. I like that. So when did you get involved in in real estate investing? So I it was right after I graduated from college. I was doing door to door sales and all throughout college and my roommate was doing lease options. He was trying to do a little bit of wholesaling. because his dad was into wholesaling. And he would always- What year was that?

I graduated from college in 2015. So- Okay, go on. Sorry. So all throughout college, he was trying to do real estate and I was doing door-door sales, right? And he would always be like,

hey, come and do real estate with me. And I would see that he was struggling a little bit, right? Because the inconsistency of him doing the business, right? So I was like, ah, nah, I'm good. So after I graduated from college, and by the way, door-door sales, if a lot of people don't know about it, it is lucrative.

It's a good industry. You make a lot of money doing it. But after graduating college, I didn't want to do it anymore. I didn't think it was a long-term play for me. So I thought, what would be another good option for me? So I started interviewing at other jobs, like, you know, property insurance sales, insurance, like whatever other sales jobs I could think of because I had the sales experience from door to door. And after interviewing at a couple places, I didn't really like the interview process.

I didn't like people sitting in front of someone and then basically being like, hey, you are the good fit or worthy of working for me. Because I had just worked for myself and I was my own boss at the door door sales thing. I just didn't want to do it anymore. So after a while, I was like, you know what? Forget all this interviewing stuff. I'm just going to do my own thing again. So I reached out to my buddy and I said, hey, are you still doing real estate? And he was like, no, I'm working at a tech sales company.

I was like, well, let's, how about you quit that? I'm about to quit my door door thing. let's go all in on wholesaling or we didn't even say wholesaling because I didn't know what that was. I just said let's go all in on real estate. And he's like, okay. So he quit, I quit. And then we sat together in my basement. We started trying to call for sale by owners. We didn't know what the heck we were doing, but we figured it out, right, eventually through a long story and long journey. But yes, that's how we got to talk about. Yeah, let's talk about how did you figure it out. What were your challenges in figuring it out? Oh, man. I probably made every mistake in the book because

I didn't know anything zero. I had no idea about real estate. And we were, I was really basing my knowledge on like what he knew and he didn't really know that much either. I come to, I came to found out he didn't know anything. Was the one leading. It was a blind leading to the blind.

It was. It was. We really didn't know. So we would sit there in my basement. We would call maybe 10, 20 for sale by owners. And that's just like going on Zillow. And we thought we were making a dent. Right.

We were like, oh yeah, we're doing, we're doing business. And it was nerve wrecking. I came from sales, but I was, I was scared. I didn't know what to say when I was talking to people. I had no idea how to even have that conversation. So we were both like not doing enough.

And eventually we were like, hey, you know, we probably got to get some other people involved who know what they're doing. So we made some Facebook posts looking to network with people who were in real estate. So he made a Facebook post saying, hey, look in a network with someone that, you know, is interested in wholesaling or knows about it. We would like to chat with you. And one of his friends worked for. a broker who was interested in wholesaling, right? So the broker at a brokerage, he just didn't know a ton

about wholesaling, but he wanted to get into it. So one day me and him, me and Corey went and sat down with his broker, and he's like, hey, guys, I just had a dream. I had a dream that I got into wholesaling in Missouri and started wholesaling properties. And Corey's dad, originally, he was the one that was wholesaling that got Corey into it. He was from Missouri. So we're like, oh, man, this this lines up this is kind of interesting you had a dream about wholesale Missouri cori's dad does it maybe we should figure out like working together so he's like hey look I got some cubicles in my brokerage you guys can I got a dialer I got some lists you guys if you just hammer through those those leads expired listings you know just almost calling the phone

book he had a bunch of lists that just weren't that good right but um he's like call through these if you get any wholesale deals you keep them but if you have any listing given to me and I'll give you a percentage or I'll give you a split of what I can get you on the commission. So that's how we got our start. We started cold calling, call calling eight hours a day, did it for three months, eventually got our first deal, which was a $5,000 pre-foreclosure, a guy that was an expired listing that was in pre-foreclosure, eventually got that deal. And that one was a complete mess, got called into the board of realtors, even though I wasn't a realtor. They called me in because they thought I was doing something scammy. Yeah, and I didn't know what they were talking

about when I went and sat down with them. They had a tape recorder. They were recording us, me and Corey, and we didn't know what was going on. But, you know, that deal was not very easy, but it went through. Then we just failed forward. We got, then we got another deal. I think we ended up doing like $96,000 in the first six months. It was just constant grinding.

He was calling. It was knocking doors. We would go knock doors and look for people, ask them if they want to sell. And just constantly grinding. And then after six months, months after making 96k, we ended up spending all of it on mailers that did not pan out to deal. So we like went back down to zero, had to figure it out again. Like it was just a constant roller coaster ride of trying to learn how to do this business

effectively and efficiently. If you were to grade, Nathan, like it would take 10 actions to get one result. How would you say like when you started how many. actions you thought it would take to get that result versus how many actions it did take to get that result. Oh, man. Well, you know, like a percentage wise. Yeah, I would say in the beginning, I thought maybe like without having any knowledge, I thought like I could get it done with like 50% effort maybe if I go by effort. But it took like like 500%. It took way more than what I thought, you know, to get a deal. Okay. Every single time I've answered that question, Nathan, I've gotten

same answer. Yeah. And you just gave me the same answer. I'm going to answer it differently. And the answer I always get is 10 X. 10x. Yeah, right. All right. And, you know, 50% versus 500%, that's 10x. Like literally, you nailed it. But every single time that I've asked that question of somebody, it's without fail. It took me 10 times more time, more effort, more headache, more heartache, more money, more failure, more learning than what I ever anticipated just to get to zero. Would you say that the way I'm saying that, you know, is about accurate? Yeah, it is accurate. It's interesting because it's like you want to be good at anything you pursue,

but you really are unaware of the amount of effort it takes to succeed, right? What do they call that? It's called like uninformed optimism. That's what I think most people have. I have my board right back here. You don't see it. It says blind optimism. There it is.

That's it. Yeah. Yeah. So I call it blind. It's interesting. and you bring it up because this is one of my whiteboards behind me that you can't see, but blind optimism. And so what,

and I want the people listening to your story right now to relate to that because maybe someone's listening to this right now and they're having that struggle and it's a lot harder than what they expected, right? And they're starting to feel like I suck at it. Like you're starting to have that self-talk, you know, that self-doubt that, you know, lack in the confidence that you could get you to the next step, right? And I want the audience to realize what, whatever you think this is, multiply it by 10, and that's your starting point.

And it's consistent across all these conversations that I've had. Nathan, what's one specific thing? So you're talking about the journey being from the real estate board, you and your partner, making $96,000 and going to zero because you got a bad, you know, plan with the mailers. What did you learn specifically from those experiences that the audience could avoid the mistakes that you and I have made in front of them? Man, there's so many. So many problems that I would never have done again.

Like with wholesaling specifically, like the negotiation process, you know, I didn't really know how to find the best buyers. But let's not even talk about wholesaling specifically. Let's just talk about your business in general. I think trying to do something and not having the right people on your corner in the beginning, it's going to take like 10 times longer. It's going to take a lot longer than if you can have like a mentor, if you're going to help somebody has experience.

Like I thought Corey, my business partner at the time, had the experience, but he didn't. So we were really just flying blind. And even with the broker, he had experience with listings and stuff like that. But he did not with wholesaling. So we were really just trying to figure it out. And we were losing, right, a lot when we probably couldn't, didn't have to face that much heartache or that much pain if we had the right person, right? You were right people in our corner.

Whether that be a mentor, a partner, a colleague, or whatever. It doesn't mean sort of matter how that person shows up. but success leaves clues and so does failure. And I can tell you that, you know, I've been, I've been in business for many decades. And what comes as natural and easy for me today 20 years ago was a freaking challenge. Yeah. And so if I would have had, I just had a lunch earlier today with a 22 year old gentleman who I,

I'm his favorite fan. I'm his advocate. And I'm, I'm thinking, I didn't say this to him, right? But I'm thinking like, man, if I had the advice. of me at 52 years old when I was 22 years old, my goodness, I could have just freaking shortcutted a whole bunch of heartache and headache, but I didn't have the wisdom to seek that person. That person existed back then and it exists today. It's just having the wisdom to know, hey, I got to go find that person. You know, the tough thing about even getting align yourself

with someone that has that wisdom is like sometimes you don't really understand or can't really comprehend what they're saying until you make those mistakes as well. Because I've had mentors have said, like, don't do this and I do it anyway, you know, or I do it. I don't think, I don't know, maybe I just am not at that level where I really understand it. Does that make sense? Like, even if someone tells you. Yes. And when I had that experience, you know, as a younger business person myself, and that is a trait

that will drive us to be successful, but it can also get in our way. And the trait is, it's like, I can figure out anything. Yeah. And that's, that's the confidence that you have within yourself. and that confidence is what's going to get you there, right? But then there's also to sit there and say, how can I put my ego aside? How can I put my confidence aside?

How can I put, like, I know how to do this and I can figure it out? How can I put that aside for the purpose of examining what's in my blind spots? And, you know, and I don't know if sharing it in the way that I'm sharing it right now, but I was in, you know, as a 30-year-old, I would not listen to the 50-year-old guy. I knew better. Yeah, he doesn't know, right? Like, that was my confidence. And that confidence served me well.

But man, you know, I could have saved a lot of challenges by, you know, putting that ego aside and embracing that I did not know everything. Yeah. And another thing that's difficult when you're not experienced is you don't ask the right questions either, right? Like maybe they do know, like how to avoid certain things or the right advice to give you, but you didn't ask the right questions and maybe they didn't look into the business, your business deep enough. For example, like this is a flip.

During COVID, during the pandemic, we were flipping a lot, right? and we were feeling good like oh everything was selling so we decided to structure like a creative financing deal with this seller and we structured the terms what we thought what we understood would make sense and we had mentors at that point but we just didn't ask

hey mentor does this make sense to structure like this so what ended up happening is the deal didn't work out we didn't have the paperwork set up the right way where we could fight it in court but then after all that happened he's like oh you should have done this And then it's like, oh, that would have solved that, but we, we didn't even know to ask that question. So that's kind of the hard part about having like mentors is you just sometimes you don't know the

right questions to ask. Here's the cool thing is when I didn't have the tools that you and I have today back then to ask better questions. And I would suggest anybody listening to this right now to ask yourself to go to chat GPT or Gemini or whatever your, your AI, you know, tool is that you enjoy using and ask the question, which is, what questions am I not asking? What am I not thinking about, right? Like, so we have, yeah, like, like, but you have to do that.

You do. Right. And then, and then understanding that what am I not seeing? What's in my blind spot? Who do I need? Like, those types of questions to be able to help you to know the right questions to ask. Without that tool, it's near impossible. But the fortunate thing is, is the tools are there today.

Exactly. I would say that that's huge, right? It's like the blind. And that's what, like, I would say going back to the mentor thing is like they can see those blind spots, but obviously that they I would do a great job as well. But that's the tough thing is the blind spot. That's why I think that's what experience gives you is the ability to see, not have as many blind spots. I think there's a greater thing with experience as well, not just to reduce the blind spots, but to have an awareness that there are blind spots.

And then a maturity to, you know, going back to what we're talking about, which is, you know, aligning yourself with the right people to align yourself with people that have it doesn't have to be more experienced but different experiences that may understand that perhaps you're a very logical person right but you scare people because of your intensity right and you could solve problems and you know i'm probably describing at least one of the two of us here in the room right now but you don't have the ability to be able to really understand the emotional impact that you have in in your communications. Somebody that's really in tune with their emotions may be able to bring that out of you. And that's something that's not like a tactical type business thing, but it's so vital to understand how you show up in the world to others. If you have a strength, you probably have an equal weakness to whatever strength that you have and just have an awareness of that. Nathan, what are your goals? What are you up to today? Pass forward to today. Man, the type of goals that I've set for myself have changed over the years. Like when I first started,

I read a book called Traction. I don't know if you've ever heard of it by Gino Wickman or something like that. But like I used to set goals that would be like five years out, 10 years out, like for business. Now to be honest, I just I just do my best. I attack bottlenecks to my business and I'm always looking to improve and get better. But I don't really have business goals. I used to. I used to like I said, I used to plan out.

But now it's like, hey, let's let's make the product better. Let's make the service better. if we're around in a year, great. If we're not, we'll pivot and we'll change and we'll go to the next thing. So that's when it comes to business goals. When it comes to family, oh, man, yeah, like spend as much time as I came with family. I'm completely debt-free right now, so that's a goal I hit. Let, you know, goals stay healthy, do good.

I do Brazilian jiu-jitsu. I want to get better at that. I like to read a lot. So my goals have always continued to read and improve myself as a person and to serve and just love others. That's like, that's all my goals. It's just to, honestly, like, if you want to get religious, it's just to be like Jesus. That's my ultimate goal. That's all I care about.

That's fantastic that you share it in that perspective. For business goals, I got, because you talk about five, 10 year goals, for me, early in my business, also had five, 10, 20 year goals. And they didn't really work for me. What worked for me and what I've done probably for now 15 years or so, I say five cycles of this is three year goals. And the reason why a three year goal really works well for me personally, and it's not about, like, I'm not to suggest anybody follow this, but if it works, follow it. But you got to find your own deal, right? You have to find what works for you. For me, it's a three year journey because it's close enough that I know that it's not like La La Land future.

I'm never going to get there, which was like a 10 year journey. It's just too far out. but long enough to actually get something significantly significantly impactful done. Right. And so that's where for me, it's I've lived my business life in three-year cycles. And in three years with intention and focus, man, you can get a lot done. I agree. And then you add up like in my case over the last, I've been in business much longer than 15 years,

but I've been doing that cycle for around 15 years. And then you add up, you know, five cycles of that. that that's 15 years, but I know if I would have had a 15 year goal, I never would have hit it because it would have always been too far out. It's just, it's not manageable, but I find three years is manageable. No, I agree. For my goal setting, what I like to do, and I'm sure you do it too when you reverse engineer, but I break it down into quarter, quarterly goals, and then I get a year goal and then a life, like a life ultimate vision mission plan. And then it reverse engineers into like this year, what am I going to do each quarter? What am I going to do

each month, week, day. So I have goals. It's just not like we discussed, right? The big long ones, those are tough. What's been your biggest challenge in business? Man, my biggest challenge in business has probably been being willing to market. Like for my industry, you need a market. Like marketing is huge, right?

And for me, it's spending enough in marketing. But I always like teeter between like, do I want to spend more to generate more leaves to generate more stuff in order to generate the revenue or I'm okay with where I'm at. That's, that's kind of my, that's been the toughest thing. Because I know if I spent more, I'd make more money, but then it comes in, there's just more problems that come with those bottlenecks. So it's that. That's it.

That's the problem. Marketing. Got it. And so it's like, how do you manage the flow of, I would say this with marketing. It's like you want one more coming in the door than what you can get to. Like if I'm going to spend $1,000 on a market initiative, 10,000, 100, whatever the case may be, and I need,

you know, 10 pieces of business to be able to sustain my lifestyle and what I want, then whatever I'm generating has got to be 11. And now I know, like,

I can feel comfortable and confident that I'm good to go and I also have choices. Because I can fire at least, I could fire at least one client and still hit my goals. Yeah. You know,

it's been kind of interesting for me and my journey is like, my, the lifestyle that I've created through like wholesaling in my business right now. I'm not saying like I'm set and I never have to work again, but my lifestyle is like very, I live a very inexpensive lifestyle. I live on a farm. My expense are super cheap. I'm deaf free. So it's like it's really hard for me to like stretch to like just get

more more, more, more money, more money. It's like I'm good. You know, I just, I get to spend my time with my family. I, uh, you know, I work when I want, wherever I want. It's so it's, do you know what I mean? Like, so it's that desire to do more and more and more. It just don't, it doesn't really drive me like it used to when I was younger. Right. I love it. I love it. I love that you have a great perspective of life.

As we finish up, what's a piece of advice that you could give to that person getting out of college right now, considering entrepreneurship, business ownership, creating and designing their own life, maybe even wholesaling as a specific niche? What advice would you give them? So number one is like get realistic on like how much it's going to take like we've been talking about, like how much effort is going to require. And if you're willing to do that much effort to get what you want, right? Like there's a guy, there's a Greek philosopher.

I really like. His name is Epictetus or Epictetus. I don't know how to say it. But basically says like if you want to be an Olympic champion, this is back in the day with the Greeks, the philosophers. It's like if you want to be an Olympic champion, first consider what it takes to be an Olympic champion. Yes, everybody wants to be an Olympic champion, but consider you got to stay up late.

You got to work. You've got to die. You got to do all these things. Like, are you willing to pay the, the price to get what you want. So that'd be my first thing is like, make sure you're willing to pay the price. If you want freedom, if you want to, you have tons of money, wherever you want, like, are you willing to pay the price to get it? So it's number one, like have a real conversation with yourself. And then number two is like align yourself with someone who's done it already and learn

from them. That's it. Those two things. Great piece. Great piece of advice. Nathan. How can somebody get in touch with you? If you're interested in learning how to wholesale real estate and make money in real estate with the yeah as a beginner or as if someone that wants to uh increase their portfolio or fix and flip and learn how to get into real estate uh just go to my website it's painless flipping dot com as it's uh not pa i it's pa y and e like my last name my name's nathan pain so it's painless flipping dot com you can book a call directly if you just go to that site and we can chat and i can point you in the right direction or i can work with you but that's uh that's the best way to get holding me. Thank you, Nathan. And thank you for your time today and sharing your words of wisdom.

Audience, have the best day you like. Be grateful, make good choices. Help somebody. And God bless you. I love you guys to death. See you. If you're a real estate agent averaging four to 12 closings a year, and you want to know what it looks like to join a team that sets your appointments, handles all your administrative task and gives you daily live training. Visit www.com.com. for slash join us. Nobrook months.com for slash join us. We review every application.