Right About Now - Legendary Business Advice
Founder Lessons From Scaling, Going Public, and Rebuilding | Rick Jordan
23 Jun 2026
Transcript generated automatically by AI and may contain errors.
Chapter 1: What lessons did Rick Jordan learn from taking his company public?
Let me tell you the biggest lesson that I learned is that if you have that thought cross your mind, oh, I could just go out and get this cash that puts the liability on me to put it in the company to keep it going. That's not the thing that needs to change in that moment. The cash flow into the company is not the thing that needs to change.
It's the company itself, something within the company and how you got to that place to begin with is where the change needs to happen first.
you don't win by following the playbook you win by rewriting it 700 episodes deep with the people who actually built something real no theory no fluff no shortcuts this is right about now with ryan alford
What's up, guys? Welcome to Right About Now. On today's episode, we talk to Rick Jordan. He's back on Right About Now, and this time we're getting into what happens after the big climb. Rick took his company public. They scaled fast. They fell harder. Acquisitions can be tough. You got to rebuild. You got to live through the pressure.
Today, we're talking failure, ego, resilience, and what it really takes to get back up when you run out of that rocket fuel and you got to get up and give it your own. Rick, welcome to Right About Now. What's shaking?
dude it's good to be here again man you had already done a lot and taken off but you're about to go towards this climb and you've had it whatever stage of that there is you know i want you to share that we all see and hear people talk think that they won't be subject to things that others have the failures the wins the highs and the lows i even put people sometimes in that it's always highs for them never lows it's always yeah no joke they're always crushing it yeah
And then it's like, well, why can't I be like them? Right. Exactly. We all have that a little bit. I try to live in my own lane. I do that pretty well. But at the same time, we all go through it. I'm excited for you to share a little bit of that. And I know we'll get into some rosier things. Just share what that journey has been like the last few years. I started an I.T.
business 16 years ago now, and I got it to the point where it was doing a few million per year. And then I had gotten it to a few, meaning like four million per year.
four million a year is a lot to a lot of people truly i thought it was a lot to me 15 years ago then in a matter of two year time period i took it from four million to 15 in just two years it was right about that time that we went public and that was through some m&a through some acquisitions because i had built this thing you know the movie the founder with michael keaton one of my favorites ever right and michael keaton is playing the role of ray crock from
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Chapter 2: How did acquisitions impact Rick's company's growth and challenges?
It was also the stock price, of course, because that kind of follows the hate that comes after that. And I burrowed inside of me for a little while. What could I have done differently? Where did I mess up? That's something I've always done. I've never been the blame guy to push it on other people. I've never played the role of the victim. And that's not just in business. It's in relationships.
It's in every aspect of my life. It's always, I turn inward and it's like, where did I go wrong first? I kept getting the same answer, even from mentors, investors that were in the company, or even guys on my board, Kevin Harrington from Shark Tank, or David Meltzer from Jerry Maguire.
All these guys are in my circles and literally on the board, and they're like, we don't see anything that you did wrong. Do you know how hard it is to accept that? You want to blame something, and it starts at the top usually, but... Sometimes it doesn't when it gets bigger than yourself. As we're recording this, there's going to be some really bad tornadoes that are sweeping through Chicago.
Part of my titles would be like storm chaser. I do actually literally chase them if you want to call it a hobby of mine. But that was going to be my first career when I was seven, by the way. Seven years old, I wanted to be a storm chaser. I still do it. If you're like me, you probably spend a lot of time paying attention to what's happening in the world.
Markets, business, crypto, interest rates, sports, politics, all of it. I'm always looking at headlines thinking, okay, what happens next? That's honestly why I've been spending time on Gemini predictions. What makes it interesting is instead of just watching stories move the market in real time, you can actually trade on the outcomes of real world events.
Maybe it's oil prices, what happens with the Fed, crypto movements, major sports events, or broader world headlines. There are live contracts across all kinds of categories. And what I like is it feels built for people who already think this way.
If you naturally pay attention to trends, follow business news, or spend your day analyzing what's happening in the economy and markets, this gives you a completely different way to engage with it. The platform itself is also really straightforward. Everything runs directly through the Gemini app. The interface is clean, and there are new markets opening every day.
I've been on there browsing different contracts, and it's honestly just fun seeing how quickly things shift based on real-world news and momentum. And again, it's not about just passively watching headlines anymore. You can actually participate in what you think happens next. To start trading right now, head to Gemini.com slash predictions and browse through all available contracts.
If you're like me, you probably spend a lot of time paying attention to what's happening in the world. Markets, business, crypto, interest rates, sports, politics, all of it. I'm always looking at headlines thinking, okay, what happens next? That's honestly why I've been spending time on Gemini predictions.
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Chapter 3: What hidden problems can arise from acquired businesses?
When they said, it's like, we don't see anything you did wrong. Well, maybe it's kind of like a tornado. If you have your house, you can't just pick up and move your house to try to get it out of the way of this thing. It's hitting it no matter what.
It's the best thing that made sense to me, seriously, because like, even though you might see that the clouds are kind of dark and everything, but it could only be a half a mile down the road is actually where this destructive force is. And you still just can't see it yet. And you're praying it doesn't hit you. Yeah, exactly. You see signs.
I saw signs ahead of time before this stuff really came crashing down. And that's the thing you start to like pick up. He's like, is this really happening? You start investigations and then that takes a little bit of time, a month or two months or whatever. Remember, all this took place in a matter of six months when it came crashing down. It happens really, really quick.
You spend 15 years building something and then it can crash in six months when it does. This is the part that I was getting at. And of course, shareholders, they don't understand they need to play victim. Seriously, I'm sure a lot are going to be seeing this and I don't care. I know that I've done everything.
This is exactly what happened, but it doesn't matter because people lost their investment. They lost the money that was put into it. Hey, if you looked at the filings, I have put over 2 million of my own, my hard money into this organization. Going public and afterwards, I'm still the biggest investor. I'm the lead investor in myself. And I haven't gotten that stuff back yet.
It's like, so what do you think I'm going to do, man? Do you think after this tornado hit that I'm just going to sit in the rubble and throw my hands up and be like, well, I guess this is my home now. I landed in shit. You're going to get out as fast as you can. It does. It takes time to rebuild that stuff. That's the mode that I'm in right now. It's been great.
I look back and if I visualize the rubble of a house completely destroyed by a tornado, that really sucked. I hope that's never going to happen again. But you know what? Maybe this time I'm not going to use a wood frame. Maybe I'll use steel beams or something like that. Fortify this sucker like it was in the middle of Florida facing a category five hurricane.
The thing doesn't just utterly destroyed like that. You built up a couple million, four million, and you took it to 15. And I get you start scaling. You do M&A and you scale. It's curious to me that how it becomes zero. You built it alone before you went public and all that. Why is it zero? Is there nothing to carve out of this thing? It didn't go to zero. It went to two. Built it up to four.
Then M&A and going public got it up to 15 in a matter of two years, right? From the four to the 15 and then six months and went down to two, which is where we're at right now. Most of the customers that were part of these acquisitions were just gone as well because of the results, the aftermath of a lot of these things. That was all disclosed.
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Chapter 4: How can founders effectively handle the emotional burden of failure?
So then they were servicing customers, the public company, but that actually became like a vendor client relationship. And those transactions were fully audited so that they stayed at an arm's length because interrelated company transactions are never that great.
When it comes to being a public company, that's why we made sure we did everything right in that and kept everything completely separate, all the transactions completely logged. If there was services in essence being provided, there was invoices that were going back and forth, man.
So in essence, it's like my private company, which I retained customers and I never transferred all of them over when we went public, which is why we went down to the two. It was kind of like the go back. Exactly. Exactly. Yeah. You kept the security blanket, but you had no intent on using it. That's a good point because it was never a desire to keep those customers separate.
It was actually going to be another acquisition for us, acquiring the original customers. But then the timing in what it was, it made sense to just keep that. Let's just stop for a moment. Let's put the brakes on because we just discovered some not so great things with the people that were selling these businesses to us. Let's see where this pans out first. And then it became a blessing, dude.
Seriously, as the foundation again. And that's the part that's like, I don't know if anybody ever really goes back to zero. Do you? No, I wouldn't think so. I've had a crash and burn myself and I didn't go to zero. I mean, I lost a million dollars in the car business in 2014, but I didn't go to zero. You know, I was doing Carvana before Carvana. I had the idea, right? The execution wrong.
I didn't go public. I didn't go that far. I took all the crashing and all the burning. But not zero, right? No, not zero. And it was enough to land on my feet. And there's always another day. I feel that in you. I would have known that about you anyway. I know you well enough that I call you a friend, but obviously from a distance, we don't see each other often or anything like that.
But I know you to be a fighter and I know you to be someone that would never go to zero, not just in the bank account, but more in the aptitude and ability and the soul. I know what's there. You'll be all right. A lot of people probably relate to this conversation. We've all had failures of different scale and different sizes, and you're never immune to it. Got the t-shirt. Learn from failure.
I like to keep it raw and real, and it sucks, especially when you feel like you let people down. That does creep in too, man. I know I didn't say that in the story I was telling, but that does creep in. You and I are kindred spirits that way. How did I allow this to happen because it's affected so many? Yeah, you take it personal. Even if you couldn't change anything, it weighs on you.
It's human, but it's also human for those people that feel like, okay, well, I don't know what they would have expected you to do different. There's another thing that's a little hard for guys like us to grasp. When it comes to people that are working for you, for the majority, 99% of them, The mental point of origin is not the organization. It's themselves.
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Chapter 5: What strategies did Rick use to rebuild after setbacks?
And entrepreneurs expected to be self-sacrificing and fall on their own sword. And that's what I found is the expectation of everybody who works for you in the organization too. From founding it 15 years ago and bringing on the first employee, the very first one in 2011, who actually stayed with me through this entire thing, but then left in the middle of the stuff.
It was another hard lesson for me. And seeing that take place, it was just, I get it. I understand why everybody is in the place that they are. And at the same time, maybe I should take some cues from them in this next run. If I'm not in a good place, the organization won't be in a good place. I'm picking up what you're throwing down a little bit.
You probably wrote checks that you probably shouldn't have written.
totally yeah because you were trying to save it or do what you can you felt like it was altruistic it's the right thing to do but it actually probably wasn't for you yeah not that you're being selfish you're trying to do what you felt it was the right thing but at the same time it's not it's an interesting place to be when you've built something like you did and it's always on you i've never gone public and don't plan to like anything that i've done i've
I intentionally kept it in my own circle, my own failure, my own wins. I mean, I've got teams and all that. It would be a struggle for me. I could write that check, but I'm not going to because I can't. Like, that's just not for certain things. And unless you've done and been in those levels, you don't quite understand what the hell you're talking about. No, you just write the check.
No, no, actually, you don't write the check. That feels right, but it's not right because the company has to stand on its own. I was coaching a friend of mine the other day for the same exact thing. And it was like, yeah, he's like, I pulled money. This is a friend of mine, open a loan. That way I could put that cash into the company.
He's like, you know, I just kept trying to get it going and now it's just in a bad place. I'm like, let me tell you the biggest lesson that I learned is that if you have that thought cross your mind, like, oh, I could just go out and get this cash that puts the liability on me to put it in the company to keep it going and That's not the thing that needs to change in that moment.
The cash flow into the company is not the thing that needs to change. It's the company itself, something within the company and how you got to that place to begin with is where the change needs to happen first. Yeah, you're treating symptoms and not the disease. We got a disease and you're buying the best cough medicine on earth.
And that cough goes away for about two weeks till that next payroll comes. That's about it, dude. Seriously. You expect the things to turn around in that short period of time. You're not buying a cure. Not unless you spent that money on the fixer. But he don't exist either. He's only in movies. Talked with Rick Jordan. He is the CEO. Are we still Reach Out Digital? Yep. Reach Out Digital.
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Chapter 6: How can entrepreneurs avoid the pitfalls of rushing growth?
We could just go off and off and off these high frequencies, messages and high frequencies. They can they can download a lot of data, a lot of information in a heartbeat. It's almost like a shock value in that moment. It can wake somebody up or it can knock somebody out. It doesn't last. That effect doesn't last that long.
It's meant like if anybody's ever seen who's watching this has seen Tony Robbins or whatever, it's like there's moments he does this to intentionally where he'll pound so hard and then all of a sudden He'll bring it down to a low frequency because those are deep, just like wavelengths and literally in radio frequencies. It's these long waves that are meant to penetrate super deep.
They can go through buildings. They can go through the hardest substances and they can travel really far. And those are the sustaining things. That's another thing that I learned throughout this, too. But it's like, well, that's the vision for radio. All of these acquisitions that I was doing too, all these symbiotic things. It's like, it really kind of fits.
I used to think it all had to be the same frequency. I've changed that tune. It can all be different. You need different frequencies, but you all got to be on the same channel. How you get there. We all need to be in that channel. But the frequencies and all that are all needed because you need highs, need lows, need middles.
And that goes a lot away from diversity to talent, to skill sets, to ability. All of those can be frequency and intensity of certain things like those frequencies. But the shit don't play if it ain't on the right channel. If I'm going to stick with this vision of like the house in the rubble. I can look back and I'm like, you know what?
I guess there was some things about that house that I really didn't like anyways. I always wanted to paint that front door and change the shingles. You got a blower to clean it. You need mortar to fix it. I'm glad we could laugh about it, dude, because I mean, that's true. NBA Finals time is one of those stretches where every possession matters.
And if you're anything like me, you're not just watching the stars score, you're watching the matchups, the defensive pressure, and the hustle plays. The guys who completely swing a game with one steal. That's what makes underdogs steal the pot so fun.
There's a million-dollar pot sitting there, and all you have to do is pick the player who finishes the NBA Finals with the most steals in the series. Your picks don't even need to win. You just have to back the right thief. I love this because it makes you watch the game differently.
Start paying attention to who's jumping passing lanes, who's getting more minutes, who's guarding other teams' best player, and who has real defensive edge. Pick your player every game. Include their steals stat, and when the series ends, the steals leader is crowned. The pot gets split among everyone who called it right. The more finals games you back that player, the bigger your share.
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Chapter 7: What are the differences between stock purchases and asset purchases?
Or text H-O-P-E-N-Y-467-369. Starting something new isn't just exciting. It's honestly a little terrifying. I remember right before I launched my podcast, all those what-if thoughts creeping in. But looking back, taking that leap was one of the best decisions I've made. And I'll tell you, if your systems are clunky, everything slows down. If things are smooth, you actually keep moving.
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You get AI tools that help write product descriptions, page headlines, even clean up product photos. which saves founders a ton of time. And once you're live, Shopify handles the hard stuff. Inventory, payments, shipping, returns, all one dashboard. Instead of bouncing between different platforms, everything's just in one place, which honestly saves us a ton of time.
And that's the part people don't always see. It's not just about building a website. Start your business today with the industry's best business partner, Shopify. Start hearing... Sign up for your $1 per month trial today at shopify.com slash ryan. That's shopify.com slash ryan. What are we building different? What are we doing different?
I put out this on X a couple of weeks ago in an interview that I did. We announced the reverse split, which most investors just do not like. They think they're going to be wiped out. But in actuality, it's the thing that could potentially save them. Truly, everybody it could potentially save. That's what I'm excited about working on now.
But what I put it out there, I'm like the biggest lesson I learned from an M&A perspective is there's two types of sales, two types of acquisitions. One is where I've illustrated as a bucket. You can buy the bucket and inside the bucket are the customers, the processes, the SOPs, all the intellectual property of that business, all the tools that they use, everything.
And it's all inside this bucket. You can buy the bucket with everything in it. And that's what we did. It's called a stock sale. Or if it's an LLC, it's a whole membership interest. You take control of that entire entity. You get the EIN. It You're buying the whole thing for those.
Or the other way is that it's an asset purchase and you take what you want out of the bucket and you leave the bucket and the things you don't want with the seller. And you could even take everything out of that bucket if you wanted to. But you leave the actual bucket with the seller because on the outside of that bucket are things that are taped to it or riveted to it.
If it's a metal bucket, I always envision a metal bucket for some reason. Things like debt, accounts, payables, reputations. Exactly. Yeah, right on. Even the name of the company, the branding of that company is all part of that bucket. That's like the stickers on the outside. If you want to look at it that way, that's where I know looking back that I fucked up.
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Chapter 8: How can business owners implement scalable systems for long-term success?
And if we had done those as asset sales, we would have been free and clear. No issues. It was really the second large acquisition that we did that kind of tanked everything. It was around $5 million in revenue. And when you lose all that almost overnight, it hurts everything, man. You still have all the employees that you gained. Going from, it was probably, I think, 12 people.
We were doing $4 million a year with 12 people. And then we were doing 15 after the acquisitions with 94. That doesn't even scale right. It doesn't even make sense. That's part of the integration, though, because with any kind of acquisitions, when I said I was going to carbon copy and stamp those things, clone it, that was part of the process over the first year with these.
It was supposed to be to where we reduce the headcounts in order to make the companies more profitable and run more efficiently under my integration plan and the way that I build things. But when it happens so quick after the acquisition, it's a different story. Then you're just scrambling. You're trying to figure these things out. But yes, one of the biggest things was a sales tax liability.
This is probably the single largest one that was there. When you buy a company that's on paper showing that they're making net income $600,000 a year. After all expenses, even with the owner's salaries added back in, if it's 300K for the owners, the company was really only making 300K a year. But then these are called ad backs because you don't have that liability. Those people could go away.
The sellers could go away if they were buying the business. So it becomes future profits that are just kind of baked in. Now we're really down to 300K a year that the company was making. But then there was a sales tax liability that we did not know existed. And this is where a lot of the shareholders are like, you should have done your diligence in all of this. We did. We called the state.
We called the IRS. We got all the forms done and everything came back that they were paid. The problem is that it wasn't disclosed that a sales tax audit was in progress by the state. And that's not something that the state will ever disclose. It was only 21 days before.
So within a month before we actually closed on this, that one of the sellers signed an extension on that audit with the state and still didn't tell us. It was about five months after that acquisition that we got a phone call from the state that said, hey, we finished the audit.
But even so, like still filing sales tax returns during those time periods and nothing was ever brought up about five months later. And that was multiple six figures. So now you have this company that was producing around 600K in net income every year, minus the employee or the owner's salaries. Really, they were only making 300. And now you get this multiple six figure liability.
It makes the company worth zero out of the gate because every company is typically bought on a multiple. of EBITDA, which is their net income. In this industry, it's roughly like four to six times. You're talking three to $4 million, somewhere around there is what the company was worth in what was presented to us.
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