Episode 5

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Published on:

4th Feb 2025

Engineering Your Business for a Profitable Exit with JR Rivas

In this episode, we sit down with JR Rivas, an entrepreneur who shares his unique journey of building and preparing a business for sale.

JR discusses the strategies he employed from day one to ensure his company was attractive to buyers, including the importance of eliminating risk and understanding financials. He reflects on the lessons learned throughout the exit process, including deal fatigue and the complexities of earn-outs.

Join us as we explore JR's insights on entrepreneurship, planning for exits, and what lies ahead in his next ventures

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Transcript
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>> Lani Dickinson: JR I'm so excited to have you here today. Thanks for coming on the

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show.

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>> JR Rivas: Thank you for having me.

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>> Lani Dickinson: Yeah. tell us a little bit about

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who you are, what you do, and you've been

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on this exit journey for a good, what year?

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>> JR Rivas: More than that. So my name is JR Rivas

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We run an Airbnb done for you program

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where we handle the locating of the property and

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the interior design of the property. And

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pretty much from like a year in the journey, we

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were like, oh, I didn't even know you could sell a

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company unless it was like a multi million billion

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dollar endeavor.

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>> Lani Dickinson: Right.

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>> JR Rivas: And, so we started to ask around and talk

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to people, and I actually had a friend that sold an

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agency that had declining revenue

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and no salespeople, and they managed to

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get a seven figure offer with, 80%

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upfront. So once I heard that, I

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was like, oh, maybe I can sell a business.

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So I started talking to brokers. We

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basically started planning for the exit from

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like, nine months into starting the

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company.

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>> Lani Dickinson: Okay.

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>> JR Rivas: and our revenue had already kind of been on an upward

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trajectory. So, yeah, we

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listed the company in

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February, right at the two year mark.

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And, we entertained a lot of different offers. We were

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under contract once and then fell out,

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and now, we're under contract again.

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>> Lani Dickinson: Awesome.

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So you did it a little different than most people I

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interact with. You got the idea

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that, hey, we might be able to sell this thing

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very early in the journey. And so what

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things did you do differently? Like, well, you might not

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know, but what did you intentionally say? Okay,

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we got to do this differently because we're building this to

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sell.

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>> JR Rivas: Yeah. So I had a friend who went on Shark

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Tank and he ended up getting a deal,

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but from Mark Cuban. But in the due diligence

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process, they told him, like, yeah, we really don't want to

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do this deal. You should just sell it. I probably have a

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buyer for you. And then he sold it. And the

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buyer or Mark Cuban's team told him,

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if you would have sold this like nine months earlier, you would have gotten like

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four times the money for it. and that

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always stuck with me because by the time someone wants

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to sell, they've gone through that port, that part

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where now they're not going to get what they could have gotten

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at their peak. So that always stuck with me.

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And as entrepreneurs, we all have ideas. Like, I know I could spin

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up another business tomorrow. So I wasn't so much

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married to the idea.

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As for your question of what we did differently,

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we started to Engineer the company from a

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perspective of a buyer.

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And that was interesting because

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the biggest takeaway was that everything that a

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buyer looks for is how to eliminate risk.

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So everything that you do to get your company ready to sell

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actually makes it a better company. So you should be doing it anyways.

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and I just learned so much about what actually makes a company

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valuable by talking to these people, talking to you,

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and, just asking questions to now where I'm like, okay,

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if I were to start another company, it's probably going to be better than this. Ah. Because

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from day one, I'm going toa find recurring revenue. I'm going toa look

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for a certain cac to ltv. I'm going toa look

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for a certain, business model

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that, would appeal to. And I'm gonna know from day one,

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like, what are theyn toa say when we're at the table

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negotiating? What are they gonna say? And I'm gonna work from

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day one versus when you're already sick and tired of the

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business, which, I've kind of gotten to the point, like through

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the, exit. I've gotten to the point where I'm like, I can't wait to

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get this over. Like, I have so much deal fatigue right now

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>> Lani Dickinson: That's real deal fatigue.

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>> JR Rivas: on the calls on Poker Face. Like, I'm always like, yeah,

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ah, we'll run it for a few more years. But in the back of my mind, I'm like, I

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can't wait for this to be done.

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>> Lani Dickinson: Yeah, exactly. You hit.

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There's so much gold in what you just said. Deal

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fatigue. It is real. I often tell people,

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take calls before you're ready because of what

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you said. You don't want to plateau and then try and

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sell m People are buying cash flow,

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right? So you want to still have upward

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trajectory and, and growth that's available.

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So if you're trying to grow your company

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and be on that upward trajectory, and then you've got to

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take calls, you know, having a deal room ready and having

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other people who can participate in the calls and the

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due diligence is really important. But

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you don't know that if you haven't come into it with

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the benefit of, you know, you had a few people who had done exits, you'd been

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asking questions in reading and all of those things. So

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hopefully people like, rewind that and re listen to

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what you said because you,

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hit several really important key points there.

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when did you start? I assume you have a deal Room

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now where you have like data in the sandbox type

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of thing. When did you start that part?

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>> JR Rivas: So around the one

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year mark when we were like we're going toa try to sell at the two year

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mark we started asking, we were working

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with this guy who was like consults for you on a

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monthly basis. He's like this is what you're going to need. You need to get your

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face out of the ads. You need to show that

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someone else can do the coaching calls. You need to show that someone else can

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do xyz. You need all these management people in

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place. So we started to know

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what they were going to ask for and we started kind of putting it

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together early on so that we could get ahead of the, and not

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only get ahead of the objections but say to

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them, oh, a year ago we were doing it like this and

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in preparation for this sale we started doing it like

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thises. And that was a big, because that was a big question like why are you guys

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selling? You're at the two year mark, you're on this upward

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trajectory. So our answer was like, well we've

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always planned. This has been the plan from day one here.

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>> Lani Dickinson: Ready to sell. Yeah.

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>> JR Rivas: So I think that helped us

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out a lot.

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>> Lani Dickinson: Helps you out in the deal because

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there's. You're not a stressed out buyer who has to dump

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it.

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>> Lani Dickinson: And that answer says like we built this from day one.

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So yeah, you know, we don't need your

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desperation.

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>> JR Rivas: But we still made a lot of mistakes. Like I was telling you

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today, I didn't go to school for accounting and

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I fig I realized through this process our accounting method was

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completely wrong for our type of business

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which I've never even thought twice about in my life.

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So there's still some mistakes but next time around

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it's going toa be a lot more tidy and, and having

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your books in order and stuff like that, which we tried to do as much

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as we could but without the knowledge

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of what they're going to ask for. like what's

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an adjusting entries report? I just learned that one

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this week. What's a compilation report?

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so all these different things that now I know the next time around this is

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gonna be so m much easier.

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>> Lani Dickinson: You know what's interesting is I think there's a statistic and this

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isn't exactly accurate but it's something

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like only the Small Business association

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says only 30% of business owners get

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their financials. 5%

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do something to open and look at them.

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That doesn't say how many people take action on them,

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but the kinds of things you just talked about and

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cash based versus accrual base and all those things.

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It makes a difference if you're planning to

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sell. But how many business owners do you

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know who are just running it with a, entry level

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bookkeeper?

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>> JR Rivas: Yeah.

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>> Lani Dickinson: That's better than doing it on the back of a napkin.

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But when you get to the place where you're ready to sell, you need

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somebody who's like, how do we

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do an adjusting entries report? And what does it even

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mean?

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>> JR Rivas: Exactly.

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>> Lani Dickinson: Yeah.

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>> JR Rivas: So then it's like hours with accountants that I've

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never.

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>> Lani Dickinson: Hours and dollars.

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>> JR Rivas: Yeah. Our person never doesn't understand this stuff.

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So now I'm on upwork and I'm interviewing these people and I'm trying to find

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someone who's done this before and done this for exits. And

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you're kind of scrambling because there's all these deadlines. So.

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Yeah, it's a lot. It's a lot if you don't

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have someone holding your hand that's done this.

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>> Lani Dickinson: So last year when we met and you're like, yeah, I'm

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selling my business in February.

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>> Lani Dickinson: And I started asking you a few questions.

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Do you remember back to that moment, like, what was your biggest aha.

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Like, ooh, I might not be ready in February?

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>> JR Rivas: well, it wasn't that we weren't ready in February, it was

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that for the number that I was. For the number you

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wanted. We weren't ready and we

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didn't get that number. But we got

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very within 14% of that number.

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>> Lani Dickinson: Awesome.

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>> JR Rivas: And I'm very happy with the deal. I'm very

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happy to move on with my life. And I'm very happy

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that, like I said, I have a million ideas. So I know I'm

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gonna spend something out bigger and better. And now knowing

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what I know, the next business is gonna have all these.

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>> Lani Dickinson: I have accounting right up front.

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>> JR Rivas: Yeah. And we'renna. We'll probably exit that one. Another

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big lesson. Wait till three years if you can.

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>> Lani Dickinson: Yeah.

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>> JR Rivas: but we'll probably exit right at three years for a bigger

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multiple and with a better model, maybe less

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stress and much less stress.

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>> Lani Dickinson: So, what are the. After we talked that night, what are

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the things you like went back home and you're like, we gotta do a

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couple things different right away.

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>> JR Rivas: Yeah. So I, immediately went back home. I talked

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to my business partner. Well, I was texting him like mid

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conversation with you. I'm like, lonnie says we have to do this, Lonnie says we have

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to do that. And the biggest

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things were not

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trusting the broker 100%

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because your broker think of it as like a real estate agent.

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If you're selling your house for 600,000

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do and they have an offer for

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575 but you know, they know that they could

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get maybe 6:30 if you waited a little bit longer or

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whatever. Most likely they're gon TOA take the 575.

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So they don't necessarily have your

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best interest in mind. Although you know, they're great people, they help

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out a lot, they're very knowledgeable. But at the end of the day

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like sometimes they might steer you towards a

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deal because they know that this person has a higher

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shot of closing even though it's not the best deal. So

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you have to kind of play the game of the

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buyer and you have to play the game with the broker

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as well. And there's been times where like I tell my

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broker because I know I need, when my broker takes this to

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the seller, to the buyer, she needs conviction.

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So I give it to her as like this is a non negotiable

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when in reality it's probably not just so that

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she carries that conviction over to.

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>> Lani Dickinson: That conversation so she doesn't feel like

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we could fudge here.

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>> JR Rivas: M. Exactly.

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>> Lani Dickinson: And that's fudging with your future.

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>> JR Rivas: Exactly. So that's a big thing. you have to be

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so detail oriented because there's

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101 ways that you will get got in these

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deals.

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>> Lani Dickinson: Ye.

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>> JR Rivas: in ways that like you can't even imagine. And

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not that like business buyers are scrupulous

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or whatever, but they're business people and they've done this

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before. They have a lot of experience. They've bought

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and sold. So they know how to

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put in deal terms that are really favorable and try to

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sell them off to you as if. Oh, everybody does this.

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>> Lani Dickinson: Yeah. And you experienced that in your first offer.

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>> Lani Dickinson: Yeah. Now isn't your buyer the same buyer

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just came back and said okay,

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let's.

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>> JR Rivas: We've had many interviews. so we were under contract.

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We ended up we pulled out of that

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agreement because I didn't like. Me and

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my business partner, we didn't like the earn out portion

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and we just really felt like we weren't going to get

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the portion of the earnout.

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>> Lani Dickinson: Yeah.

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>> JR Rivas: The other thing, the other big reason we pulled out was our

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broker was charging us 10% which I

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didn't know at the time is like outrageous.

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at least for our, I don't know, maybe there's some industries, but for

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our industry that's extremely high. we've

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had offers as low as like 4% for

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brokers that were just as credibleeah. and when you're talking millions of

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dollars, that's hundreds of thousands of dollars. Makes a big

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difference, especially divided by.

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>> Lani Dickinson: Two in a partnership.

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>> JR Rivas: Yeah. So I would say, yeah,

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those were definitely some big realizations.

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>> Lani Dickinson: Yeah, so you said the big earn out

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word. So this is a big

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like, do I, don't I conversation.

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And from my perspective,

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I've been on the buyer'side you know, I've

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been on the acquisition side when I was in corporate. I've

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been on the selling side when I was trying to sell my gym before

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COVID which closed it down, so we didn't have to deal with that.

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But

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the people who come in and this is

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smaller buyers who are like, you're dealing with a buyer.

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Right. But it's also like private equity deals where they bring in

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a whole team of mergers and acquisitions peoples and lawyers and

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know people are really overwhelmed with that process.

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And everybody is trying to sell this

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idea of the earn out. And so people are like, should I

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take it? Should I not? Generally

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the earn out is the promise of what they call

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the second bite of the apple. So

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leave 5 million in and in

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three to five years we turn that into 15 million. So it

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would d be like a private equity type of a thing. I don't

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know. And you don't have to disclose your deal terms about what your earn out

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is. so it's like there's this promise of

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more at the end

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and then. And so that sounds

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attractive. You know, I leave, I roll 5 million in equity and

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in three to five years I have 15 million. Like who

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wouldn't do that deal? But the other side

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of that is the terms of how

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the earnout is earned. The seller

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often loses control of the thing that will create that

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result and they become a longer

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term employee of the business or consultant of

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the business or something. But they've lost control. And so

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oftentimes people don't end up with their earn out. I don't

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have data on when a small

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business is purchased by a single owner

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or a couple of people who buy it. How many people actually

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get their earn out? But I know on the private equity side, less

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than I think it's people.

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73% of CEOs don't make it

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to the five year period. They're ousted because they

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won't do the hard things that take it from 5, 6,

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7, 8, 9, 10%

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profit to 20, 25% profit.

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So did you and your partner,

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I know you have't earn out and you don't have to discuss the terms of

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that, but did you have to struggle with I want more cash

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up front versus I do want to

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stick around or that second bite of the apple. Sounds

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good. Walk us through what goes through

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the seller's mind and the decision to

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say, all right, finale, take her now.

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>> JR Rivas: So, the first deal I had to earn out. The second deal,

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it's like an equity earn in. I

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don't know what the VC term is for it.

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so it was a long journey with the earnout.

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number one, I feel like if you aren toa take an earn out,

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you should get at least 70% cash

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upron in my opinion. we had

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a call with this guy who had built like

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a nine figure company and sold it,

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very popular software that people have heard of.

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And he told me he was like never

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on a zoom call. He's like never taken earn out.

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All I've ever seen and done is create hard feelings and you

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never get the money. so

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once he said that, I was like, am I okay

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with getting this cash upront if I never get another dollar?

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>> Lani Dickinson: Right?

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>> JR Rivas: And the answer is yes. And

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obviously I'm sticking around. I have nothing

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planned yet after this. I'm going to help

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the buyer succeed as much as I possibly can, be

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as available as I can for him, genuinely

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help him to reach his goals.

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but I understand there's

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very specific goals to hit and maybe if we fall a little

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bit shy of that, then we might not earn the equity for that year or

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whatever. So, that's kind of how I would

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look at it. But when it's like a, well, 20% upfn

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and then if you hit this goal next year, I've also

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heard all kinds of different rounds. I had a buddy who, his earnout was based

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on maintaining 80% of the revenue.

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which he felt like the guy would have to be an idiot to

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mess that up.

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>> Lani Dickinson: Yeah.

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>> JR Rivas: so I would say it's very complex and

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there's always a lot of terms in the air andouts and definitely have a

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lawyer. That was another mistake I made. I signed an LOI without an

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attorney and because I was like, oh, it's non binding,

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but There's a clause 14 binding

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provisions. This, this and this

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are binding. so that was a whole learning

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lesson. So there's just a lot

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of missteps that you can make

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and really just understanding what's normal. Like

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maybe having another thing is I had. We've gone

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through three attorneys now. One

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worked with tech startups for the most

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part so those deals were just completely different. So he

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would throw out all this stuff and then we would take it to the

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broker and she'd be like well that's not for a

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deal like this. And then once I really asked around and

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talked to people I realized like yeah, she's probably right. And he

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was very, very aggressive. to the point where

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like we took what his

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remarks and we took it to another lawyer and the

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other lawyer was like this wouldn't kill the deal for

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me if I was on the other end. But as their lawyer

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I would say well if they're going to go this aggressive then now we have

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to go way more aggressive and then dial it back.

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So there's even a mini game to play or a side quest with

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like which lawyer you choose and what's your strategy

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and how do you think they're go goingna play ball on

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their end. So it is a real life

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game of chess, but the consequences for making

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bad decisions are high.

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>> Lani Dickinson: Yeah, no for real. And you can't go back becausee like you

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said, there's contracts and lawyers on each side ready to

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go all in. what I heard in that

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is being really clear on

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what you're okay to walk away with. And I heard that in the

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broker conversation as well. It's like here's the direction

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I gave her and she thought there was no wiggle room

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because here's the number we must

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have and then knowing that in the earn

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out that's a really great way to think about

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okay, I got toa get the number I

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need up front and then if that never

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happens I'm still in great shape for

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whatever it is the next piece of the journey is.

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I also feel like and often say the

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people who successfully make it through

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you know, a life changing exit is there re

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really clear on what the exit gets them

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in terms of life, other opportunities,

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next business, you know, whatever.

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so calling out that clarity I think is important because often people

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don't take the time to get really clear on what that is. And

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it sounds like you've done that work

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to say, you know, what does this mean and what am I really willing to

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take? So what's on the other side of exit for you? I heard

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you say, you know, I might start something else and build that for exit and do

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it different. But like in terms of what

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does this exit really create for you on a deeper level? I mean,

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yeah, another business. But like you said, you have a million ideas

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and 90% of them could work. And you know, you're smart

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and you can do that, but what does it create for you?

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>> JR Rivas: Yeah, great question.

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So, at the end of your talk yesterday,

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you basically

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in different words stated that

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after you went on this entire journey you kind of

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realize like you one, I don't know if you would call it regret or

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whatever it was. Like sometimes I think

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I should have just been on welfare so I could be with my

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kid. And if I was like

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22 that I would have been like, this is

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crazy. Like she's made so much money. Like maybe she just didn't

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make enough or whatever. Which I know you've made plenty

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enough. Plenty enough.

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>> Lani Dickinson: Yeah, it's not that.

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>> JR Rivas: but now at 30 I'm

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like, that's what I want. So I want to have

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an exit. I want to take a year or however

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much time we need to help the buyer. In the meantime,

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I want to have a kid, get married and

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take my time figuring out like take some time to

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properly invest the money. I want to give away

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a lot of it, like a big chunk for it. And I have

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some ideas for that and some people I'm working with.

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so most people's answer I think here would be like,

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well, I want to start another business. I want to invest that to 10xit or

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100x. I could, I don't know if I can curse your

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but I could give a fuck about it.

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>> Lani Dickinson: You can curse all you want.

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>> JR Rivas: I could give a fuck about a hundred xing it.

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Yeah, I think just

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optimizing for more quality of life.

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And I've fantasized about all these ideas of

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what to do. Everything from like

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building a very simple. Like I've

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built spreadsheets on how I can build a business to make a million

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dollars a year with three people. three full time

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people and down to

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like how much time it would take for each client, how

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much of my time would it take to. And I could see that being a

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thing and I think I could do that and be very comfortable.

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even if I don't get to a million ebitda, or maybe I could

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sell that. but I have some ideas that are also like big

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play too that I think could be like $100 million

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companies or like take a crack at very, very

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difficult Problems. But these are all just

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ideas swirling in my head. Like the other day, like, m. My

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girlfriend is, a PA And I said, how

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do hospitals communicate patient

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information between Hospitals's a mess. Exactly.

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>> Lani Dickinson: S a mess.

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>> JR Rivas: And I was like, that's a billion dollar idea.

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Do I want to kill myself to do that? It sounds

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exciting. It sounds amazing. I'm sure someone's thought of it.

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Someone's maybe tried it and failed. But that's a really big

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problem that you could make a billion dollars with if you could figure out how to solve.

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>> Lani Dickinson: Yeah.

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>> JR Rivas: so one day I wake up, I'm like, I wan toa do that the

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next day I'm like a, ah, two person, three

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person company with high 80%

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profit margins where I have to work five hours a week

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and I can hang out with my kid. That would be

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amazingah. and give money away and all that stuff. Hang

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out with my friends, see my family. My mom's getting

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old. I just saw her in, Tallahassee.

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>> Lani Dickinson: We'll edit that out so she doesn't hear that part.

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>> JR Rivas: She knows itah.

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>> Lani Dickinson: Okay.

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>> JR Rivas: and I'm like, you know, I see her every now and

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then, and based on life expectancy,

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I probably have like, statistically

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60 more times that I'm gonna see her.

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>> Lani Dickinson: That, hits different.

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>> JR Rivas: Exactly. So I think when I was

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younger, all I wanted to do was just make more. Make more. I bought a

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Lamborghini last year. I think around the time I met you, I bought a

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Lamborghini. I have 17 properties in

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my portfolio, a few of them over a million

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dollars each. and every time I've got acquired

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more stuff, it's just brought more,

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responsibility and never more happiness.

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So I'm like, I actually want to scale down and

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I want to maybe get a smaller place. And

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maybe the other day I was like, maybe I should buy a Prius

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or a Tesla instead of having a Lamborghini.

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>> Lani Dickinson: You can do that. Just don't get in the fast lane and go just under

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the speed limit and manage the battery life in the fast lane.

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I'm good with it. If you just were there in the slow lane.

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>> JR Rivas: Yeah. So I think most of my goals post exit are more

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around, like, who, I'll become versus, like, what

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I'll make.

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>> Lani Dickinson: Yeah.

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>> JR Rivas: And that's what I think I'm super excited about.

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>> Lani Dickinson: That's amazing. At 30 years old, you have an old

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soul.

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>> JR Rivas: Yeah. Well, I started business at 18. 18. I

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started a tax business, which technically this would be

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like my second exit because I Sold the tax

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business. But it was one of those deals that you warned people

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against. It was like an equity

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transfer or debt transfer

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seller finance deal that I never got paid on.

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but I technically exited that business and I was like

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22ah. so I started business at

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18, so now I'm 30. It's 12 years

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of grinding, hiring people.

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>> Lani Dickinson: Well, and as an entrepreneur, you, that's like dog years.

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There's no playbook and no SOP when you start like

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that. And I know that you've already done things to like take

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care of your mom and that kind of stuff and bought the house and all that

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kind of stu ###uff so, you're just an amazing

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human and I love just where your headspace is and

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I love hearing your story and like all the things you want to

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do after. It's just a pleasure

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to know you and an honor to be involved in.

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>> JR Rivas: Thank you. And thank you for all your help too.

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Like, I remember last year on the

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cruise I was like, I need to sit Lonnie next to

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Lonnie every single day. And I just asked you

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a million questions.

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>> Lani Dickinson: Do you remember when I was like, so tell me about your sales

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process. Because one of the major things is do you have consistent,

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repeatable, optimized sales process that's gonna give

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you value? And then if you also have monthly recurring

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revenue in addition to that, it's like, okay, now we're

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talking, right?

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And you were telling me like, about

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your social seller who closed most of your deals. And I'm like,

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but you're gonna have like 75

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year old guys sitting in a boardroom who've never heard

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about social sellers. And you've got to sell 17 year old in

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Canada whose mom's gonna ground him if his grades

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drop. And that's your sales. Like, do you remember

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that moment? I was dying inside, laughing.

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>> JR Rivas: So since then he actually left. Cause he turned

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18. This kid was 17, making 10 grand a

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month.

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>> Lani Dickinson: People probably thought I was kidding. They're like, he turned 18 and he

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left.

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>> JR Rivas: and then he was like, I feel like I've hit a ceiling here.

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I want to go be a closer He was just an appointment setter.

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>> Lani Dickinson: Yeah.

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>> JR Rivas: And he ended up leaving. We had figured out

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another traffic source by that time and now we got someone

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else to take over his job. So now we have two traffic sources.

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and yeah, we definitely heard you on

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that.

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>> Lani Dickinson: Yeah. Well, it's just those

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of us who live in the digital world,

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we sort of lose track of what people in the non

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digital world think about and how

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they consume. I know when I was introduced to social selling, I was

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like, these people are literally

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messaging on their phone. But you know, when I left

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corporate, it was through social sellers selling my

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product.

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>> JR Rivas: Right.

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>> Lani Dickinson: So yeah, that was really a fun night for

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me. so anyway, I'm glad you got a lot out of that. If

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people want know more about you, follow you, learn

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about your journey, where would they go?

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>> JR Rivas: so I heard recently that the highest IQ

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social media is X. So I've started

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to try to be more active on there.

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>> Lani Dickinson: Ye.

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>> JR Rivas: And so yeah, follow me on X. Just search for

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JR Rivas or Rivas on X.

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>> Lani Dickinson: Awesome. Well, thank you for being here and I can't wait to see

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what you do next.

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>> JR Rivas: Thank you.

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>> Lani Dickinson: Yeah.

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About the Podcast

Freedom To Exit
Freedom to Exit with Lani Dickinson
Freedom to Exit helps small business owners turn buyers into beggars by building sustainable, scalable, and sellable businesses—while avoiding earn-outs, seller financing, and discounted exits.

Hosted by Lani Dickinson, this podcast is for entrepreneurs who want to build a business that runs without them and sells on their terms.

Most businesses never sell. Why? Because they weren’t built to be sellable. Whether your goal is time and location freedom or a profitable exit, the steps are the same:
- Designing a scalable, self-sustaining company
- Building predictable, repeatable revenue
- Structuring your business to attract the right buyers
- Avoiding seller financing, earn-outs, and bad deals
- Understanding how buyers structure deals so you can negotiate from strength

Each week, Lani breaks down the realities of exiting a business, shares insights from top entrepreneurs and buyers, and gives you the tools to maximize your company’s value before you even think about selling.

If you want to own a business that works for you—not the other way around—Freedom to Exit will show you exactly how to get there.

About your host

Profile picture for Lani Dickinson

Lani Dickinson

Lani Dickinson is a former Fortune 175 CEO who left the corporate world to help business owners achieve what most never do—true freedom. Through STEALTH, she helps founders scale smarter, exit richer, and reclaim their lives by transforming their businesses into sellable, high-value assets.

Most entrepreneurs are trapped in a cycle of working too much and earning too little freedom. Lani’s expertise lies in building sustainable, scalable, and sellable businesses—giving founders the ability to step back, cash out, or create a legacy that lasts. If you’re ready to stop running your business and start owning your life, you’re in the right place.