How I Bootstrapped 3 Software Companies, Survived a Legal Battle, and Sold My Company

I bootstrapped three software companies at the same time. So I was a very active real estate investor. Built a huge real estate turnkey business, had property management companies and then I started selling. I actually closed one, sold one, built another one, and then was building a software for my own company. And when we did it, I was in a bunch of closed door masterminds like this, but all real estate related. I showed the data what my software did for my own brand and just gave them all of kind of like you guys do here with the business stuff. I gave them, here's, here's the blue pin print, here's how I replaced, you know, $5,000 in overhead by software Izing it, systematizing it all into a software, made it all way more efficient. Then everyone wanted it and I didn't. I'm not a software guy, so I knew nothing about software. Had a really good guy and then he, I flew out to San Diego, sat down with him, got introduced to some software people and you know, we knew there was a hey, everyone in this room wants this. But it doesn't exist. It's why I built it for me because all the software in our industry sucks compared to how we actually do business. So we, I wrote the check in 2017. Yeah, 2017, right before my son was born and started building the first software and then on the road of building that one, ended up building a second one and then the third one failed and bombed, which most softwares do. The first two took off but with a lot of blood, sweat and tears, selling off a lot of stuff along the way and selling off businesses along the way because I knew it was it. Like I had an offer right away after like the first year in business for a private equity company that wanted to just buy it. I said no because kind of like I just heard Kyle talk about he can over pitch sometimes and then the people are like, wait, my business is actually really good if you're interested at that level. I'm onto something here. And that's what happened to me in 2019. So I kept going and then I merged that company with another company to 10x, thinking we would bring the strategy together. Ended up a bad partnership which we found out through Covid how different our personalities were in stress, which is also I was coaching along the way and all of that. So yeah, that's what happened. I started it, built it and then long suffering legal battle and as I shared on stage yesterday, gained 60 pounds during that legal battle and all the stress I was going through and not Sharing with anyone, thinking I was about to lose, quote, unquote, my baby. Like, I built this software bootstrapped, brought it from nothing to multiple seven figures, merged to about to break eight, and then back up from where it's at now to where it was. So it's kind of one of those, like, how do you go, you're here and you get all the way back here out of nowhere, unexpected. Nothing you can do to control that, to. Okay, what do I really actually want to do using all the tools I shared on stage. Like, all right, let me sit back and like, literally sit with this. And said, okay, I just want to purely coach. The last year I started a test pilot of. I'm going to offer just coaching. None of my tools, none of my software. I won't do real estate. I'm just going to coach the person. And it was very successful. So I was like, okay, that's it. I'm selling. Yeah. I reached out to a bunch of people. Kyle just happened to be the actual real buyer in my mind. Right. The guy that, yeah, he talks to talk, he walks the walk. All these other people are asking me 100 more questions, but this dude buys companies, is not asking everything you are, so maybe you're not really a buyer. And he's the only one that produced an actual loi and actually closed. Well, no, there's another. I did have another loi, but I just knew he didn't.

There's a lot of people out there that are. They think they know how to buy a business. Maybe they learn to watch YouTube for an afternoon.

Yes.

There's a lot of people doing it, trying to learn on the go, but it was just different when you. When you saw Kyle or connected with Kyle.

I knew. I've seen some of his stuff just like them, but I knew from watching his mastermind and wanting to come to some of them that he actually bought businesses. Right. So he wasn't the first thought. Because I was in software world, I've reached out to other software companies in real estate. I reached out to people I knew in real estate. I've been all over real estate. So there were a couple very viable people that owned software companies that could have bought it. But that. That in itself is like, now you're. They're looking at it differently. Right. They don't really care about the IP because they have their own. They care about is the value worth buying your customer base and then pivot them over. Right. And so those deals were close, but not good enough to make sense. And Then Kyle was quick and evaluated and now that I get to watch him in his room, like say you did exactly what you tell them to do. And we went through that process and then we ended up closing and it was great.

And so you're seeing what you experienced and it's the exact same stuff, isn't it?

Yes. So I experienced as a seller being able to sell to him, move on with what I needed to move on now, being able to come speak here, but more importantly, being able to watch what's happening in the room. Like, well, what you're teaching them. I fit in that buy box. If they were. You don't say software specifically, but I fit in the buy box of the range of what you're looking for. We went through the steps that you're laying out for these people to do. You did the diligence. There's things I had to submit during that. Those things got evaluated, more questions got answered. Exactly as you lay out for them in the steps. And then we got an loi and then we did some legal documents to solidify the deal and how recent exchanged money. We just closed in February of 2024 financially. So literally, what's that? Well, what's today? August now? I think we're August 1st six months. So, yeah, less than six months because it's the middle of February when we. I think it was like Valentine's Day or the day after Valentine's Day, when the. When the wire officially hit and officially done. Now he's the majority owner of all of it. And it's his stress and his thing, which is cool because he's not stressed about it. So I also get to see how he operates now on the flip side, being a partial owner of that. And for me, the benefit is twofold because I know where he wants to take it and so I get to go along for that ride. I believe he can do that. I know that he can because that's what I would do if I was going to run 100% of that software business. And he has some relationships I didn't realize he had which are going to come in and take some key roles. And we can both already see the growth that's there. But it's exactly what he shares. I just saw him present on his 10 best strategies for buying. I fall into probably. I think it was number seven on his list. Like, well, that's number seven in his playbook. And that's why he kept me on to consult for what else he wants to do with it because he has A bigger picture over the next three to five years. And I will probably most likely exit with my ownership percentage, likely make more than I would have made in what I felt lost through the battle I went through. But more importantly for me, besides that the money's a side benefit. It's the I get to do what I want. Right. Which is, I think most sellers, they want to move on with what they want to do in life. Which he's teaching that like guys to buy box. We're buying is people who need help. Right. And I get it. I guess I get it because I've done real estate so long that so many people that don't do real estate say, how's somebody going to sell you their house dirt cheap? I don't just list it with an agent and get top dollar for the market. That sounds great. When you don't have the knowledge and you don't understand or you watch the YouTube video and logically your position and where you're at in your contacts makes sense that that wouldn't work. But the reality is there are tons of people that are in divorce and tax default and foreclosure and stressful situations and life has happens and they don't have the time to wait for the market. So they need investors to help them out of their situation or they have an immense amount of repairs they can't afford. It's no different than buying a business. You're buying a distressed business or distressed situation or just one where they want to move on and they want the fastest, easiest solution. And you guys have a really cool marketing system for how you go find those too. So from a business side, I like that.

And this happens in almost any kind of economy. I mean, this what I love about this twofold one, we're not talking about something that happened 10, 15, 20 years ago. We're talking about something that happened five months ago.

Yes.

And the fact that Kyle stood out from all the other people who were looking to buy this business or you were looking to sell it to by following a very certain process that you've seen from their side. How did you feel as the seller? How did you feel? Were you being pushed? Were you being manipulated? Manipulated? Did it feel. Was it aggravating or was this a pretty clean, transparent process with Kyle?

Yeah, it was a very clean, transparent process, which was awesome. It was smooth. There was no. There was no push. There was no, like, gotta do this, gotta move, gotta get this done. None of that. It was very. It transpired over months. And at the same time, it's not. He wasn't the only person I was talking to about selling the company. He was just the only one that now seeing it. I mean, and I understand he was literally following his steps in the process that led to the ultimate result he was after. And at no point during that was it a push or a gotta get this done. You're hurting me. No, he's the most beneficial.

Stressful.

No, it's very not stressful. The other people were very stressful. Like the other loi that I had was so stressful because he. Well, and I'm going to need these like 20 other things to put together. This other. You really don't. None of those. Actually. I'm smart enough to know I've bought businesses, I've sold businesses. Not at this kind of scale. Mine were more like, well, I have no choice but to figure it out because this, I need to buy this partner out of this one to move it over to here. And yeah, we need to merge. So we'll call some attorneys and figure it out. Right. Like, so it's a little different, like evaluation style, more gut than step by step process. But it was very smooth. All of the other people, like you could just tell either one they didn't have a process and made it. It was evident that they didn't know what they were doing. Or I think you said it earlier, they were. They watched some YouTubes. Maybe they have bought a business, but they bought it like I did. Right. Which is like, we're just gonna figure it out. Like, we probably need some professionals to handle this. We probably need someone to do this. He just, hey, and next we're gonna do this. And next we're gonna do this. And. Okay, we got that. Cool. Next, we need this. And this is what we're going to do next. So there's a path. He could just follow it. There's no stress for him or for me. And the other side, the most stressful was the other loi. I had probably three iterations in the loi. Like, dude, that's not what we said. So first of all, I'm not going to sign that. And your thing is asking me 20 more questions that don't have any relevancy to anything on this document. So do you even know what you're doing? Well, I don't know if I can get the month. Well, let's start there. You don't even have the money to buy the business to begin with. So what's the point? Like, I'm not gonna answer 50 more questions for you. That's. There's some digging involved.

Talking about waste of time.

Yeah, that's frustration and stress. Very frustrated, Very stressful. Luckily, I had Kyle on the other side, which was like, well, this is kind of going easy. So I would love to sell to a real estate guy, but I am very open to selling to a business guy.

Let's keep going.

My biggest concern was my customers that had been there and were loyal. Like, I just. I want to sell. I want to move on and do what I do best. But at the same token, I want these people to be left in good hands. Right. I don't want the software to like, oh, someone bought it and now they don't care and the software is destroyed and these customers got to go figure out life. I mean, some of these people have had our software for six or seven years, so they use it updated, kept up. Yes. I had a thing. There's a reason they stayed here for six or seven years. Like, you've got to continue that. Right. Which in and on Kyle's side and his things. He knows that, which is why I'm still part of his. The only demand he had after our phone calls and diligence and smooth. Which was not, like, demanding or like he said, hey, based on everything you just said and everything, you know, I want to do the deal, but only if you stay on as part of the deal. You don't have to do anything. We'll completely remove you. You just get equity and profit. But we want to be able to ask you questions and pick your brain on what you already know from being in the trenches. Well, I mean, that makes total sense. Why wouldn't I want to. And we're going to exit later, so you'll get a percentage of that, too. Sounds good to me. I don't have to do anything. I get what I want today and I get paid more later. Probably. Whether that happens or not really doesn't matter. But of course, it'll be a great benefit in the end and make all the suffering previously well worth it.

Well, and you're also. You're seeing the growth. Right. Five months in and you're already saying, you know, hey, I'm seeing this trajectory. He's doing exactly what he said he was going to do.

Oh, yeah. Within weeks of the transaction, he had already further laid out his plan and gave me names of the people that he was going to partner with to bring on. But it was going to take. We thought it would be like, next month. It'll happen. But those people Weren't available for several months to line everything up. But just as soon as I knew them, like, dude, I'd know who all of them are. If I had the ability to even do what you're doing in one phone call, I would have already done that. There was no way I could have made that connection. But that you're probably going to 10x the software overnight with the one relationship. Because I know what they have and what they bring to the plate. I would have loved to have done that. That's exactly what I would love as a part of it.

You're still doing it. I mean, you're still. Along with the. Right.

I get the benefit.

Win, win, Beautiful win, win.

It's a great win, win.

You've been trying to get to the event dates haven't worked out because you do a lot of venture coaching. Now. Someone coming to this event and from someone that just sold a business with Kyle, he's not leaving anything out here, is he? He's going through step by step. Any.

Yes, if anything, I would say from someone who's been to tons of masterminds, tons of events, tons of business things, this is one of the best I've ever seen, if not the best from a larger scale, but even so, like, because there's levels in segmentation to, like, people who have been here for a while and have learned the basics and are doing it and buying businesses now, let's take you even further in everything else that matters besides just buying the business. And I've never seen that, like, ever. One of the nutrition coaches that he just brought in to help people with nutrition. Like, people may tell you, you should go get that stuff done. Kyle's actually getting it done on site. And having someone here to answer all your questions and you're not paying for it. That's just like, hey, I want you to have this. I'm gonna make you do it by providing it and removing all the obstacles to get it done. On the flip side, I get to walk over and see the newer people who are Lear. Like, the things every step we went through. Like, I said, oh, I'm. I was number seven on there. Yep. We started there at number three on that page. Yep. I fit into that buy box example right here. It's why he liked it the most, because you could grab and put people in place. Like, I fit into every one of the steps. And he's. There's nothing left out. There's literally like, hey. And you say this to find the lead and you send out this email to get them. And here's the data scrubbing thing that we do that. And you can use us or not. Here's the thing to go do it yourself. We have our own, of course, but this we use too. And here's one that you have access to and go, go get. So go do it on your own. Here's how you do it. Here's what you say, here's why it works. Here's the data we have behind it to show you. We just did it last week. And here's the leads we got yesterday. I mean, he's literally live pulling up. This is what we did yesterday. Here's what we did tomorrow. Oh, tomorrow we're going to talk about deals and pitch them to funds, and we're going to talk to the fun guy, and we're going to talk to the legal guy, and you're going to talk to the tax guy. And there's, there's literally, if anything, you. You, you get such a picture that you go, I'm either the person that already, that's the missing piece I needed, and now I know why it didn't work before, and I can go do it and I can do it on my own and you can leave here empowered to do that, or you say, yeah, I'm gonna need to be around here longer because you already have it all figured out. And I'm not gonna figure none of this out. I'm just gonna follow your lead and work with you on doing it.

Expand a little bit on that. Bringing your coaching business a little bit. Right. So you were on stage and you weren't talking about the transactional side of it. You're talking about coaching the person.

Yes.

That these. And we kind of looked at it as protecting the profit.

Yes.

Because it seems like. And maybe you can answer this. There's a lot of things that people know they should do, and they don't do it until they've gotten themselves financially together.

Yes. Most people, including myself, will put off till. Till I'm this. Till I have that, until I get here, then I will do these things. And the reality is, well, to become or to be or to have what it is you want, you ha. You have to. If you choose to be that now and start doing those things at the level that you can do them. People make it overwhelming that, well, I worry about my health. When I can get my blood work done, I can hire the nutritionist, I can hire the trainer. So if I just focus on making more money, I'll improve my health in my Experience that can happen rarely. And what most likely happens is most entrepreneurs. And part of why Kyle had me come in, and I love it because it was just another perspective of, yeah, I spoke to a room about. I spent two hours on stage not talking about a deal at all, right. Instead, talking about your number one asset and your number one liability isn't the business that you're buying. Your number one asset and your number one liability is the thing that you have control over every day, all day, and it's you like so. And he values that so much that that's why he asked me to come speak. Hey, can you come speak about that? Because that's how you protect profits. If you protect you, your number one asset, your number one liability, you shore up the liabilities, you improve the asset in you, well, then your profits are automatically protected. Your wealth is improved, your health is improved, your relationships at home are improved. And most people, yeah, they pursue. And I did it too, right? Like I pursued in building all those businesses. Business let me make more money because then we can take trips, I can buy better food, I can get chefs, I can hire better trainers. I can do all these things. Yet I'm losing my health along the way. I'm on the verge of divorce and don't even know it. Because I think that we're good. Because I'm protecting and I'm providing, and I'm hard charging to go make the money and take care of my family. And they've got to understand. No, they don't. That you didn't ask them if that's what they wanted the ride for, which they don't. If you ask them, they wanted the quality of time that you are saying you can't provide until you get here. The reality is you can provide that now. And the funny part is you will actually get here faster with less stress and much more ease in your life. But we are lied to in life. We're programmed to believe that's not true. What we see on social media makes us think that they got here by hustle and grind and they didn't.

That's incredible.

Yeah.

Really sums up a lot of what. Why people come back to this event.

Oh, man. I spoke. Ran into the gym late last night with a guy that's been here for years who. He didn't see the presentation, but everything he asked me was like, yeah, I wish you'd have been in the room, dude. Because every single thing you're literally sharing with me right now is I addressed it and helped with, let me give you some pointers from that. He's like, wow, yeah. But he keeps coming back because he's already bought. I think he's going to talk about it because he told me he's in the middle of another transaction right now. His name's Chris. He's in the middle of another plumbing transaction and another business that he's buying and has friends that he's created in the room that have bought other businesses too. And they all have similar patterns and have gone through similar things. And for me, I have a different perspective from coaching that. Yeah, I, I know that you all just think that you're different. You're not. And then when you get in a room of like minded people and you start to be vulnerable and more importantly, I think what makes that happen in this room that people miss in other rooms is it's the leader. So Kyle's not telling you to do something that he's not doing. He's living it and then he's leading by what he lives, which allows his vulnerability to become your vulnerability, which allows you to get further in life because you're going to do the things your leader, quote unquote is doing. Where most other rooms and why I'm not in most of those other rooms anymore or I leave after a certain amount of time is that it's very clear they don't, they don't live what they're preaching or teaching. And so, you know, there's, there's inauthenticity about that and everyone can feel it. You know, it's just a matter of time, of when you'll say enough is enough.

I'll put you on the spot for a minute. If there's anything you want to say to Kyle, that's Kyle.

Kyle. Love you, brother. This has been an amazing journey. It was an amazing thing to go through the process and transaction and looking forward to our business relationship and all our businesses and super grateful that you had me come out here and speak to your people. Extremely grateful to be able to hang out with the elite wealth club and experience all the things and learn all of the stuff that you do behind the scenes. Amazing, powerful and appreciate what you're doing for people in general which will have profound impact in communities and families all over the world as a result. Thanks, brother.