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Wholesaling & Flipping Houses: Lessons from Jamie Davis

By September 11, 2025Real Estate Pros Show

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Show Summary

In this episode of the Investor Fuel Podcast, host Michelle Kesil interviews Jamie Davis, a former teacher turned real estate investor. Jamie shares his journey from education to investing, discussing his first deals, marketing strategies, and the importance of mentorship and support systems. He emphasizes the need for balance between business and family life while building relationships in the industry. Jamie’s story is one of growth, learning, and the power of connecting with others in the real estate space.

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    Investor Fuel Show Transcript:

    Jamie D (00:00)
    We were on a family vacation in Florida. It was the week before I was going back to school, kind of dreading it.

    ⁓ My bestie and I snuck away for coffee and I looked over and I saw these two gentlemen and I told my bestie I’m like I bet they come here once a month and I’m like I’m gonna go ask him what they do. I can never do what they do. So sure enough an hour and a half conversation later that gentleman told me he was a real estate investor explained what he did ⁓ and a year later I called him up.

    I said, I quit teaching, I quit coaching, ⁓ could you help me out? So he did.

    Michelle Kesil (02:11)
    Hey everybody, welcome to the Investor Fuel Podcast. I’m your host, Michelle Kesil and today I’m joined by someone I’ve been looking forward to chatting with, Jamie Davis, who’s been making serious moves in the investing space. So, to have you on the show today, Jamie. I think our listeners are really going to take something away from how you’re approaching

    starting your investing business, wholesaling, yeah, and the journey that you’ve had transitioning from a teacher to investor. So excited to dive in with all of that.

    Jamie D (02:49)
    Thanks for having me.

    Michelle Kesil (02:51)
    Awesome. So just first off for those who are not familiar with you and your world yet, can you give a short version of what your main focus is?

    Jamie D (03:00)
    Yeah, I would say ⁓ my main focus is just to grow in the real estate investing world. ⁓ I was a teacher for 18 years, so that’s a big part of who I was. That was my identity for so long. And the last two years, I figured out that, real estate investing ⁓ has just allowed a huge opportunity of growth that I’m super excited about. ⁓ I wholesaled my first

    two years or 18 months, guess you could say. And finally, I’m wrapping up my first flip and just the opportunity to not only wholesale, but also to flip projects. I finally feel like I’m a real true real estate investor. So it’s kind of fun to see the journey along the way. So I’ll continue to wholesale when the opportunity arises, but I really enjoy flipping as well because I feel like it offers a lot of the same ⁓

    The same aspects as it did as a teacher, you’re leading. I was also a coach, basketball coach, so you’re leading, you’re guiding, you’re encouraging, you’re on task, you’re structured, so it’s a lot of the same things.

    Michelle Kesil (04:06)
    Amazing. love that. And what markets are you working in?

    Jamie D (04:11)
    So currently I’m in Omaha, Nebraska and dab a little bit into Council Bluffs, Iowa and Lincoln, Nebraska as well.

    Michelle Kesil (04:21)
    Amazing. So yeah, how did you get started with investing? Like what sparked the desire to get into this space?

    Jamie D (04:22)
    Thanks for watching!

    Well, as you ⁓ go through a career for so long, I was always that person that would drive by an abandoned house and I’d be like, my gosh, whoever buys that is gonna just really transform it and most likely make a lot of money. And I really wasn’t even aware of the real estate investment world. ⁓ Every summer around August, I knew I was gonna have to go back to teaching and it was just kind of the last seven years I’m like,

    There’s got to be something else out there. I dived into possibly staying a daycare. I dived into possibly being ⁓ an insurance agent. Like just what could I, my gifts offer?

    We were on a family vacation in Florida. It was the week before I was going back to school, kind of dreading it.

    ⁓ My bestie and I snuck away for coffee and I looked over and I saw these two gentlemen and I told my bestie I’m like I bet they come here once a month and I’m like I’m gonna go ask him what they do. I can never do what they do. So sure enough an hour and a half conversation later that gentleman told me he was a real estate investor explained what he did ⁓ and a year later I called him up.

    I said, I quit teaching, I quit coaching, ⁓ could you help me out? So he did.

    And I started ⁓ getting deals by Uber driving and putting up Bandit signs and door knocking on foreclosures. And basically he said, do this. And I was like, what? You want me to do what? So I finally found out I specialize in helping people that are in foreclosure.

    Just the ability to help them figure out and give them options has been just a blessing. And so it’s kind of a crazy story, but yeah, it was based on taking a chance and talking to a gentleman in a coffee shop.

    Michelle Kesil (07:10)
    Wow, I love that. That’s so inspiring and just shows that, yeah, the right people will come into your path when you’re ready to take those leaps.

    Jamie D (07:21)
    Yeah. And lo and behold, that person is now actually one of my business partners. So he’s actually marketing in Omaha and we’re doing business together. So he helped me on my first flip. So it’s been definitely a blessing and it’s like my business is called Connect the Dots Consulting. ⁓ Just because I’m always, I just feel like I’m always connecting the dots. So.

    Michelle Kesil (07:21)
    So, yeah.

    ⁓ wow.

    Jamie D (07:45)
    God strategically places me in the perfect time, the perfect place, the perfect time with the perfect people and miracles happen every day.

    Michelle Kesil (07:52)
    I love that. That’s so beautiful. That’s very inspiring. ⁓ So yeah, how did like your first deals go? How did that process go from like knocking on those foreclosures into fully selling and working with these deals?

    Jamie D (08:14)
    Well, I would say my first deal, like I was seriously Uber driving and my mentor at the time told me I needed to get out Bandit signs. I had to Google what Bandit signs were. I had no idea.

    Michelle Kesil (08:24)
    Yeah, what is that?

    Jamie D (08:26)
    ⁓ Just a yellow sign with a H sticks that says, know, three beds, two baths. And how do you get sellers? And he didn’t know the market because he lives in a different state. So he’s like, this is how I did it. So I, my first deal was in a small town, Pacific Junction. That deal, I made about eight grand on it, but it took six months to close. ⁓ I learned what…

    a judicial state was, a non-judicial state, a divorce, just absolutely everything that could have gone wrong, but also right. I just learned a ton on that. That was my first deal from the Bandit sign.

    And then my next deal, it was door knocking. So I knocked on the pre-foreclosures and help them understand their options. I knocked on the next door neighbor’s door to get…

    I was being nosy. was like, hey, I’m here to help this person. And that ended up turning into just a really big blessing because I was able to help that family out. They were about to lose their house. They had equity in their house, but they didn’t want to stay. ⁓ So I worked with an end buyer. At that time, I honestly didn’t know how to analyze a deal. So just the ability to connect people and partner with an end buyer from the get-go, he walked it with me and is like, hey, this is a good price. ⁓ And so that was really fun.

    to be able to help that person out and not lowball them, but still give them an opportunity to start over. ⁓ That’s a huge passion of mine. I know that sometimes people walk away with not as much money as they could possibly get. ⁓ And so I just always keep the main thing, the main thing, and make sure everyone wins in the situation. And that’s how I know it’s a successful deal.

    Michelle Kesil (10:43)
    Yeah, that’s so important. Thank you for sharing that. So let me ask you this, why are you most focused on solving or scaling to next?

    Jamie D (10:53)
    I’d say right now just like the marketing. ⁓ One of the programs that I joined, ⁓ it always stuck to me when like 90 % of the time that you should be spending on is finding deals. ⁓ When we’re not finding those deals, nothing can really happen. ⁓ As well as just don’t let the market control you, but you control the market.

    And I think that is just, that’s something that I’m really ⁓ focusing in on is just being creative. Because in my mind, I do think that teacher mindset like somebody is going to buy that house. So who’s going to buy it? Is it on a creative financing option, seller financing? Is it a wholesale? Is it a fix and flip? Is it a rental? Is it a BRRR? ⁓

    So being able to continue to find the deals, working on my marketing plan, being strategic about that with direct mail, pay per click, and then ⁓ just really analyzing the deal and being able to know when to walk away from it ⁓ and then when to just pull the trigger and go for it.

    Michelle Kesil (11:59)
    Yeah, that’s so important. And so what would you say is kind of like those criteria’s when you’re analyzing the deals, ⁓ which ones are the ones that you’re going to go for and which ones maybe aren’t the right fit for you?

    Jamie D (12:02)
    Thank

    The ones that are going to make money. Those are the ones that we’re going for. Yeah, and so it’s just it’s been I think my biggest breaking point is like one of my strengths is I have the ability to raise capital and I didn’t even know it like there’s just been so many things that have just kind of been shoved in my life. I’m like, that’s good.

    Michelle Kesil (12:17)
    Yeah, simple.

    Jamie D (12:38)
    Like, I have somebody that has an extra million dollars lying around that they want to use with me. I have this. And so I was finally able to put that to work. ⁓ once I saw that, like I helped fund my first three deals that I was a part of.

    I was like, why are they, I’m just getting a point or two points. Like what is going on? So to see that has been pretty awesome and it was game changer. And I was like, no longer am going to use my private funds for other people’s deals. We’re going to use them for myself. And so just making sure that the numbers work with the market, especially on a flip, if I can make X amount on this first one, there’s definitely a big cushion.

    where even if we broke even, was just the biggest learning experience ever. yeah. So, burring it, refinancing it, that’s always the best part. I would jump into any seller financing deal that I could. ⁓ I actually walked away, I scared a lady, because I was like, a full outy in your house. And then I talked to her about seller financing and the opportunity for her to, you

    get interest rather than the bank and she was really excited and then I called her two days later and she’s like, I go, so what do you think? And she’s like, I sold it. I go, what do you mean you sold it? She goes, I took a $5,000 or less offer. I’m like, what? She goes, you started talking about seller financing. I was like, and I scared her. So that was something where it’s like just the right time and the right place to bring that up and to.

    just really make sure that people understand it. ⁓ So I’m all open for just, like I said, any deal is a deal if it makes sense. So just being creative and figuring out what fits best would work for us.

    Michelle Kesil (14:27)
    Yeah,

    yeah, absolutely. I love that perspective. So everyone I know has moments in their business where things get more real. Maybe a deal goes sideways or you have to make a fast pivot. Would you mind sharing one of those moments that you’ve experienced?

    Jamie D (15:27)
    I would just say we’re dealing with like the probates right now, like getting a house under contract and realizing that it has to go through probate. And just the ability to follow through. I think it’s pretty easy for people. ⁓ you mean I have to go through this and then they might just like shove it to the side and not follow through. So I just think that.

    My intentionality to always put the people first, the seller first, like they want to sell that house. Like no matter what, like I would love to be that person to hold their hand along the way. And so just for me being new, ⁓ I feel like there’s, you know, about a hundred new vocabulary words every single day, even though I’ve been doing this for a little less than two years, there’s new vocab words every single day, new learning. And so I’m just surrounded by great people.

    ⁓ I got the opportunity to go to a conference in Dallas and listen to Mike’s panel of speakers and I was like just so empowered when I left. But just surrounding yourself by the right people to get you through those deals where you do have to take a pivot. Because I can’t do it by myself. I need to rely on my team of people and those people that have experience and they’ve been through it. ⁓

    I feel very fortunate even on this first flip I would have gentlemen that have been in the business that just walk through that house just to make sure things are done correctly. So to have that support system has been extremely helpful. So hopefully we’ll just continue that through this deal that I have going on right now that has to go through probate. Just making sure I listen to those that have been through it and do what they say.

    Michelle Kesil (17:10)
    Totally, think mentorship and support systems is everything because there’s so much to learn and if someone’s already walked that path then they can offer that wisdom. So important.

    Jamie D (17:23)
    Absolutely.

    Yeah.

    Michelle Kesil (17:25)
    Yeah, so

    where do you see your business heading? What are some of those bigger goals that you have?

    Jamie D (17:34)
    I would say my goal, I I would like to close more consistent deals each month to have more income that, you know, just letting my business work for me, right? ⁓ Just how can I continue to allow my business to run while I’m chasing kids all over the summer at AAU basketball tournaments? So it’s just, you know, getting those procedures in place.

    So that way when things are, you when I’m picking my kids up at two ⁓ for school, that things can still run. And I’ve seen that happen. And it’s been intentional, but not like I’ve dabbed into a lot of the beginning steps and success has been happening. But it’s like, wow, if I really double down and actually run the business, how a business should be run and just be full throttle, like I’m…

    going to be exciting to see where it goes. I read the book Gap Selling. I think it was Gap Selling. I can’t remember. It was a book and it talked about just where you see yourself. And there were three couples that went on a couple’s vacation. And all three of them were pretty wealthy. And it just really stuck to me because they all wanted to stay an extra week. And of course, they have to check with the families.

    So the first family was, ⁓ they could stay an extra week because they didn’t have this empire and they had systems in place. The second family, ⁓ I don’t know, they were a little bit more wealthy but yeah, we could probably wing it. The third family ⁓ had the empire at home and they couldn’t stay because they had to get back to their empire. And I just wanna always remember that.

    The time and freedom that real estate investing has provided me is something like I never want to get to that empire where I can’t have the time and freedom that I’ve experienced. So whatever that looks like for me, yes, I have my goals, but just making sure to keep the main thing the main thing and that I’m not so much sucked into my business that I can’t pay attention to my kids and be with my family. So what does that look like for me? ⁓

    I just always know if I’m having to do things and it’s taking away time from my family then we need to figure out how to make that work and get a better system for that.

    Michelle Kesil (19:53)
    I think that’s so important to really look at that bigger why you’re doing this and know that it’s like comes down to those values of time and freedom and family. Amazing. So when it comes to building relationships and growing your network, what do you feel has made the biggest difference for you?

    Jamie D (20:05)
    Yeah, absolutely.

    I would say being personable, ⁓ even having some of those cold calls, like just cold calling people or calling, you know, warm leads. I truly just, I’m myself. I don’t follow a script. read the room, try to figure out, know, hi, this might be kind of an awkward conversation. However, are you interested in selling your property? You know, and just reading the room and I would say,

    Very few times I’ve had bad encounters with people and my conversations to these people ⁓ last maybe 20 minutes as opposed to 30 seconds. But at the end of the day, I usually end up getting somebody to say, wow, thank you for having a personable conversation. Thank you for sharing with me why I’m getting these mailers every single, why are people sending me letters that want to buy my house?

    So just being relational, intentional about the people first, that’s who I am and that’s who I’m always gonna be and I wanna always be that person that can set myself apart from other people and it’s not just a random person calling.

    Michelle Kesil (21:27)
    Yeah, absolutely. Relationships and being personal is so important in this space.

    Jamie D (21:32)
    Yeah.

    Michelle Kesil (21:33)
    So before we wrap up here, someone wants to reach out, connect, collaborate, learn more from you, where is the best place that they can find you?

    Jamie D (21:43)
    I mean, you could go to connectthedotconsult.com or you can give me a call 402-740-6044. ⁓ We’re always looking to help people in honestly any situation when they have to be forced with making the decision to sell their house. And if it’s not me that buys it, I’ll connect them with an investor that does. ⁓ Or I can give them multiple resources and actually.

    give that peace and calm that they can actually make a decision in their own space rather than being forced to do something. So those are the people that I love to help and so they can always just give me a phone call or send me an email. Jamie at connectthedotconsult.com.

    Michelle Kesil (22:26)
    Perfect, well listen, I appreciate your time, your story and perspective. Thank you again for being here.

    Jamie D (22:29)
    shit

    Yeah, thank you for having me.

    Michelle Kesil (22:34)
    Absolutely. And for those of you that are tuning in, if you got value from this, make sure that you’ve subscribed. We have more conversations coming with operators just like Jamie, who are building real businesses. And we’ll see you all on our next episode.

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