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In this episode, we had the privilege of having Mr. Rick Jordan. A magnetic CEO whose ascent to the zenith of success was forged through unwavering determination and a treasury of hard-earned wisdom.
Rick’s journey reads like a saga of triumph, highlighted by appearances on nationwide networks including CBS, Fox, NewsNation, and Cheddar, solidifying his status as a sought-after personality in the business realm. As the founder of ReachOut, Rick’s efforts took the company from its startup phase to a publicly traded entity, an accomplishment achieved without the reliance on external funding from private equity firms.
Throughout our captivating conversation, Rick generously shared invaluable insights on various pivotal aspects of his journey to success. One highlight was his deep dive into the business framework that catapulted ReachOut to the organization that it is today. His strategic approach, encompassing innovative methodologies and a relentless focus on execution, served as a blueprint for entrepreneurial success.
We also talked about investor’s self-limiting beliefs and mindset. Rick delved into the psychology that often hampers investors, exploring the subtle yet potent barriers that hinder their success. His keen observations illuminated the significance of mindset in navigating the volatile landscape of investments.
In This Episode
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His company’s journey from startup to a publicly traded company
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Recognition and overcoming of self-imposed limitations for investor’s confident decision-making
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The importance of a transformative mindset in navigating current market fluctuations
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His daily routines and productivity hacks optimizing efficiency and time management
Welcome to another episode of Wealth Strategy Secrets. In this episode, we had the privilege of hosting Rick Jordan. Rick’s journey is a remarkable saga, highlighted by appearances on major networks such as CBS, Fox, and Cheddar, solidifying his reputation as a highly sought-after figure in the business world.
As the founder of ReachOut, Rick took his company from a startup to a publicly traded entity—a feat he accomplished without relying on external funding from private equity firms. During our conversation, Rick shared invaluable insights into his journey to success. We discussed topics ranging from investors’ self-limiting beliefs and mindset to the psychology that can hold investors back, as Rick explored the subtle yet powerful barriers that can hinder success. Hope you enjoy the show. Rick, welcome. It’s great to have you here.
What’s shaking, Dave? It’s good to be here.
Fantastic to have you on, Rick. I know our audience will enjoy this one and get fired up. To kick things off, why don’t you tell everyone how your entrepreneurial journey began? It’s quite an inspiring progression.
You say “Tell everybody how I got here”—where is ‘here? I think I’m still figuring that out, honestly.
It’s true, right? The journey never really ends; we’re always evolving. Stopping means getting trapped by your goals rather than growing beyond them. And listening to your story, I know you’ve come a long way, including building a public company.”
Thank you! Exactly, “Where is here?” is a question I’ve been pondering, especially since the company went public just a few weeks ago. I remember being in Vegas at Blue Wire Studios, filming Office Hours with David Meltzer. We were interviewing incredible guests like Randy Jackson and Rick Macci, which was surreal. During a break between interviews, I got a notification that the wire transfer was complete, and ReachOut had gone public right there, in the middle of filming.
It was such an odd feeling—I looked over at Dave and said, ‘Dude, we’re public!’ He was thrilled, but for me, it was just another moment in the journey. I went right back to the interview, and the milestone sort of blended into the ongoing experience.
Wow, that’s amazing. You’re right—it’s all part of the journey, and there’s always the next milestone. Going public was just one step; what comes next?
Exactly. In the next few years, maybe even sooner, we plan to up-list to Nasdaq, which will be another huge milestone. But these are just markers along the way, from where I started—growing up poor, losing my dad at sixteen, working as the first Geek Squad agent in Chicago, and then launching a business as a solopreneur. It’s been a mind-blowing path.
That’s incredible. Can you walk us through that trajectory? How did you get your start in entrepreneurship, and what were some of the pivotal moments with ReachOut?
Absolutely. The journey started, funnily enough, because I was laid off. Best Buy was downsizing its B2B department, which I’d helped build, including writing the sales playbook. They wanted to become a value-added reseller (VAR) for business IT equipment, but eventually, they stopped offering those services. So, from that point, I started ReachOut as a one-man operation. And, well, here we are.
It’s not the type of thing you see in big-box stores on street corners in most cities. This was a very different mindset and a different market they were trying to tap into. I wrote the sales playbook to teach all the consultants how to sell these services, drawing from my background in sales that goes way back—even to my first job at RadioShack, where I was a young store manager at just 18. But honestly, I always say my sales career started even earlier, at McDonald’s.
As I’ve mentioned in one of my podcast episodes, the ‘god of all sales questions’ is ‘Do you want fries with that?’ Anytime a customer would come through the drive-thru or to the counter, whether they ordered just a Coke or a burger, we’d always ask, ‘Do you want fries with that?’ It was all about asking for the order but also adding an upsell—and it’s what taught me the basics of sales. It’s really that simple: if you ask for the order first, then follow with the upsell, you’re bound to increase your revenue.
Retaining and growing within your customer base is far easier and less expensive than signing on new customers, though new customers are, of course, the lifeblood of any business. It’s a bit of a paradox, but both are crucial and work together. My entrepreneurial journey started before I founded ReachOut, and I don’t often share this part.
You’re lucky today, Dave—I’ll talk about it here. Right out of high school, I wanted a business with recurring revenue. This was around 1999, or 2000, a couple of years after high school. I was 19 or 20 and had learned HTML during the dotcom boom. I went to a boot camp to study networking on Linux and eventually started a web hosting and web design company. I saw web hosting as a way to create recurring income.
At that time, though, I was working with commoditized, low-priced services and didn’t fully understand the concept of saturated markets. I was 19—I just didn’t grasp that yet. I signed a few customers, but at its peak, that business probably brought in about $400 a month. So, I kept working as a project manager and eventually became the first Geek Squad agent in Chicago.
I ultimately shut down the hosting business because it wasn’t generating enough revenue. But even then, I knew I wanted to build something that would provide consistent, recurring income each month—a lifestyle business, in essence.
When Best Buy laid off 700 people from their B2B initiative, ‘Best Buy for Business,’ I saw my chance. I immediately started signing clients in the IT space. Our industry has a concept called ‘break-fix’: if it breaks, you fix it, and you get paid. It’s really that simple.
If a computer’s slow, you speed it up. If it has ransomware, you remove it. But that’s not a sustainable business model. I like to affectionately call this the ‘plumbing’ side of the IT industry—not to disparage plumbers, who do amazing work I couldn’t do.
But in IT, it’s similar to plumbing because you typically only call a plumber when something breaks. You don’t usually have a monthly subscription to a plumber; they’ll come out for new construction or repairs when needed. It’s the same in IT consulting: we set up new systems, and then, when they break, clients call us back. But that’s not scalable. Recurring revenue through managed services is the way to go.
Through the years, I learned that ultra-premium services are key, especially now that I’m involved in the capital markets. Recurring revenue is incredibly valuable. In fact, you can leverage recurring revenue to take on debt. For those aiming to build wealth, understanding this is crucial: recurring revenue can be collateralized, and that debt can be used to acquire more revenue.
That ties into our investment thesis as well, which focuses on creating predictable, passive income streams. Passive investing provides a reliable income, even if the economy takes a downturn. It’s the same in business—you want that predictability to scale and grow.
I’ve made my own mistakes over the years. I had a consulting business with massive fluctuations because it lacked recurring revenue. It’s a vital lesson. Many in the technology space, especially IT consultants, focus on free or low-cost, one-time software purchases. I noticed this when Microsoft shifted Office products—like Word and Excel—from a one-time purchase to a subscription model. Now, you can’t just buy Microsoft Word once and own it forever; it’s subscription-based. This shift reflects consumer and spending trends that more people in the industry need to understand. Recurring revenue is the way forward.
This even applies to investments. Take Airbnb, for example. Rather than buying a property outright for passive income, some people lease an apartment and then rent it out on Airbnb. They generate revenue without owning the asset.
They’re not purchasing the property outright; instead, they’re paying for it almost like a subscription, in the form of a lease. Then, they use a cost-plus model by listing it on Airbnb, creating their recurring revenue stream. It’s a fascinating approach. I wish more people in my industry would catch onto this concept. For listeners, it’s worth considering as well, especially given today’s high interest rates. Buying hard assets might not be the smartest move right now; there are other ways to leverage capital.
I love that because, in both investing and entrepreneurship, so much comes down to financial engineering. Sometimes, you put together deals that others wouldn’t even think of by combining four or five elements uniquely. That’s how you create a business model, a revenue stream, or something that moves you forward. Thinking creatively and strategically can align with your goals.
I wanted to pivot and discuss your focus on mindset, which has played such a big role in your success. Could you share some insights on your journey, or key methods and frameworks you incorporate into your day?
This is top of mind because I was just having a conversation about it. In business, there are a few different levels. First, there’s the solopreneur route. As a solopreneur, you’ll never generate substantial wealth or the cash flow needed to let your money work for you. Then there’s the ‘lifestyle business,’ where you may have a few employees, and the business provides everything you want for today.
You might drive a nice car, have a beautiful home, and live comfortably. But a lifestyle business isn’t built to last, especially without a strategic exit. With around half a million in revenue, you might net about $250,000 annually—enough for a good life today, but not enough to build long-term wealth.
When you get closer to retirement, you’ll start asking if you want to keep grinding at the same level. The third level is scaling. Scaling a business is less about your lifestyle and more about creating an entity that benefits others.
When you shift your mindset from ‘me’ to ‘we,’ you’re building something bigger than yourself. As the saying goes, ‘You can go fast on your own, but you can go far with others.’ That’s the difference between a lifestyle business and a business built to scale.
This shift in mindset is one reason I took my company public and began acquiring others. Many lifestyle businesses underpay their staff because the owner takes most of the profits. But when you build a community within your organization, people feel part of a mission. My company grew from just me to a dozen people three years ago, and with our recent acquisitions, we’re close to 100 employees. We’re on track to double or even triple that by the end of 2024.
The journey never really ends; we’re always evolving. Stopping means getting trapped by your goals rather than growing beyond them.
Creating a great workplace culture—where employees are enthusiastic about the mission and leave positive reviews—is key. It’s about making the organization bigger than yourself. Ironically, when you focus on others, you end up getting what you want as a byproduct. As you build this ‘beast’ of a business that helps others, it starts to take on a life of its own.
You reach a point where you can invest in the things you want, and you have more free cash flow to make solid investments. The middle-ground lifestyle business simply doesn’t have the free cash flow to build significant wealth; true investment opportunities are typically available only to those with a higher net worth.
For sure. The visual that comes to mind is Kiyosaki’s cash flow quadrant. On the left-hand side, you can earn money as a W-2 employee, make an active income, or be self-employed, like a dentist who doesn’t make money unless they’re there. On the right side of the quadrant, there’s the professional investor, which is where we focus—creating passive income. Then there’s building a business system that runs with or without you.
I align with that. What’s interesting, though, is if you look at the statistics, only a small percentage of small businesses grow beyond 1-2 employees or reach over a million in revenue. And even fewer make it to public company status or achieve 8-9 figure revenue. What do you think holds people back from reaching that next level?
It’s often self-limiting beliefs. Many entrepreneurs set goals like, “I want to be here in a year or five years.” But every time I’ve set those goals, I usually get there faster and wonder, “Why didn’t I aim higher?” It’s not that I’m particularly talented; it’s just that once I commit, it’s going to happen.
There’s no “trying.” That’s why my show is called “All In.” It’s about giving everything you’ve got every day. Some days, you only have 40% to give, but if you give all of that 40%, that’s still “all in” for that day. On other days, you’ll have 100%. On down days, don’t lose sight of where you want to be.
I challenge everyone listening: when you set a goal, multiply it by 10 immediately. Whether it’s the number of employees, an investment size, whatever it is, aim higher. One of my coaches taught me to solve problems as if you’re already at the next level. If you’re making six figures, think like a seven-figure company; if you’re at seven figures, think like an eight-figure company. By solving for the next tier, you place yourself ahead.
I practice this in my life, taking on challenges that push me to the next level. It’s different from “hustle culture,” which focuses on endless grinding. Where’s the fun in that? Are you going to grind until you’re 65, 75, or even 80? That’s a lifestyle business, not something scalable. There’s a difference between hard work and grinding. I work hard every day, but if you’re prideful about the grind itself, you’re missing out.
Our culture rewards busyness. People often say, “I’m really busy,” as if it’s a badge of honor. But look at what people like Elon Musk or Richard Branson accomplish with multiple companies. How “busy” are we? It’s about priorities and being intentional with your time.
Rick, let’s dive into the mindset aspect, because what you’ve accomplished—starting a company and taking it public—is extraordinary. Outside of tactics, what has it taken for you to have that 10x mindset?
It’s a process. And if I’m honest, I’m rarely focused on the present moment. As soon as something’s accomplished, I’m already asking, “What’s next?” It’s a constant drive for the next stage, and learning to balance that has been key.
That’s the question I’m always challenging myself with. It’s a good thing, but sometimes I’ve had to correct myself and say, “Wait, there are still things to accomplish right now.” Staying in the future too much can be toxic. But thinking of solving larger problems as if they’re happening now—that’s the right approach.
Looking back, it took over 10 years to get to the point of taking the company public, which, from what I’m told, is pretty standard. A decade is typical for companies that achieve this. I realized that this “overnight success” that took 10 years is normal. I think it was Daymond John who said that, or I may have heard him say it elsewhere. That was the case here.
I had to go through every phase of business development that I mentioned earlier—from solopreneur to a lifestyle business, and finally into scaling. It was a constant learning process. After getting laid off from Best Buy, even though I still shop there, I made a choice. I decided I didn’t want anyone else to control my income or my lifestyle. Not in a toxic way, but because I wanted full control.
The next question for me was, “How do I make this a great place for others too?” When I used to process payroll myself, I loved hitting that submit button and seeing the positive impact I was making on people’s lives. If we had a good month or quarter, we’d reward the team. It wasn’t just about the annual reviews or pay increases; it was about constant feedback. When people performed well over time, they’d see bonuses show up on their checks. We have defined incentives, but there’s always extra because we’re all moving toward the same goal. That’s something I love doing.
Going back to that journey, I didn’t start the company thinking it would go public. My initial goal was just to provide for my newborn twins when I had no income. Then, as the business grew, I realized I needed to bring on people and delegate. I’ve never had an issue with letting go. A lot of entrepreneurs struggle with control, but I believe some people can do things better than I can. Even if they can do 70% of what I can, it’s worth giving it to them. Sure, they might mess up a few times, but they’ll learn and improve.
I stayed in that lifestyle business phase for about four years because it felt good. Money was rolling in, and there was a good amount of cash in the bank, with plenty of cushion. I had about 10 months’ worth of cash on hand for operating expenses, which is a dream for any business—to have that much cash in reserve. It meant that if all revenue stopped today, we could still pay our team and cover expenses for 10 months. But I thought, “This is too comfortable, man. This can’t be it for me.” That’s when I started asking, “What’s next after this?”
That four-year period was comfortable—almost too comfortable—and that’s a trap. I want to tell your listeners that even with investments, it’s wise to spread risk across high- and low-risk options, depending on your stage in life. I was still young at the time—44 now, so I’ve still got a lot of business left in me. But when I was 34, during that comfortable phase, I realized I needed more risk to keep growing.
What are your top three personal productivity go-to’s?
My top three are:
- Morning Routine – I do the same thing every morning: wake up, eat breakfast, work out immediately, then shower and start my day. It’s about a three-hour routine. Some people say they can’t eat before working out, but if you look at Tim Ferriss’s “30-30-30” rule—30 grams of protein within 30 minutes of waking up, and 30 minutes of exercise—it makes a lot of sense. It’s the fastest way to burn fat without using muscle as fuel.
- Top Five List – I write down the five things I need to get done that day. This concept came from Andy Frisella’s “Rule the Day.” These five tasks can range from a simple “get a birthday gift for my kid” to “review certification for a new stock series.” Both are equally important and writing them down keeps me focused on what matters.
- Quick Hits – This is my productivity hack. I start my workday with “quick hits,” which are up to 10 tasks that take no more than five minutes each. These might be a text message, a quick email, a call, or a small task that keeps others moving. It’s designed to eliminate bottlenecks and keep projects flowing. Traditional advice says to tackle the hardest task first, but if that task takes hours and other people are waiting on a simple email, you’re missing the boat. Doing these quick hits first thing creates momentum, helping me feel accomplished and eliminating procrastination.
That’s powerful.
Yes, and it puts you in a winning mindset. I remember a VC from Ireland once said to me, “You Americans spend a lot of time just ‘faffing about’ in companies.” In corporate America, there’s a lot of busy work that doesn’t move the ball forward. But if you start with meaningful tasks and quick hits, by 10 a.m., you’ve already won the day. It gives you freedom and flexibility and kills procrastination. The key is the discipline to make that first-hour count.
And coming back to wealth strategy for the listeners, I think it’s really important to treat your investing with the same focus, attention, and follow-through as you would a business. You can’t just set it and forget it. If you want to take a hands-off approach, then you might as well just hire a financial planner and outsource your financial life.
But in reality, you’re building a team of professionals around you, setting goals just like you would for a business. You need to define where you want to be, what you want to do, and what you want to have. And then, you should regularly check in to make sure you’re on track—doing goal-setting exercises, making quick hits, and taking action to accomplish those goals.
Those are the people who succeed. Those are the ones who rise above. Rick, if you could give the listeners one piece of advice on how they could accelerate their wealth trajectory, what would it be?
One of the best things that’s accessible to anyone at any stage—and I’m a full proponent of this—is an IUL, an Indexed Universal Life policy. I don’t sell these, but I truly believe in them. They take advantage of compound interest. When I first got into this, it wasn’t the main thing building my wealth, but now, it’s one of the key drivers. Of course, what I’m doing in the public markets and the capital market space is important too.
Growth isn’t about grinding harder; it’s about thinking bigger and smarter.
But the IUL is going to completely cover all of my expenses by the time I turn 65. I wish I had understood this concept earlier. There’s a component of premium financing on these things, which is incredible. Let me throw out some numbers for you.
I started when I was 40, and now, four years in, I’m just a few years into a seven-year term. At the end of 10 years, the policy will have $10 million in it. By the time I’m 65, that number jumps to around $39 million. I can draw about half a million a year from it, and it will continue to compound. If I live to be 100 or older, that could be over $100 million. And all of this can be passed down to up to two generations.
To premium finance at this level, you need to have at least a $5 million net worth. That’s one big reason you need to build a valuable lifestyle business or investment portfolio to get to this point. Once you’re there, you can take advantage of this.
That being said, even a decade ago, I could have achieved this level without premium financing, especially if I had started while I was still in the lifestyle business phase or the solopreneur phase of my company. It would have just had more time to grow because of the power of compound interest.
I don’t think this is something that will make you wealthy overnight, but it will give you freedom as you age—freedom from worrying about money. And isn’t that wealth in itself? To me, that’s true wealth: the freedom to have everything taken care of.
Being really rich is the freedom of having everthing taken care of.
Rick, you’re completely speaking my language. We are licensed, and we help our clients set up whole life insurance policies because it’s one of the cornerstones of how the ultra-wealthy deploy capital.
If you have capital sitting in a bank right now, and you’re paying attention to what’s happening in the banking industry, you know that your money isn’t safe in the banks. Mutual life insurance companies have been around for over 150 years, since the Civil War, and they’ve seen countless recessions. Your principal is as safe as it gets.
And then, of course, there are all the other benefits you’ve mentioned—tax-free compounding, creating an income stream later in life, and so much more. Another huge benefit that I wish I had when I was running my first business is that it gives you liquidity. I’ve had some bad quarters in my business, and how nice would it have been to say, “I don’t need to pay myself right now because I have 10 or 20 months of liquidity in my life insurance policy.” That’s super powerful.
Now is the time to shore up your capital. If anyone has questions, please reach out. Rick, it’s been a pleasure speaking with you. You’ve provided some insightful advice to entrepreneurs out there—helping them think bigger about what’s possible, both from a wealth and entrepreneurial perspective. If people want to check out your podcast or learn more about what you’re doing, what’s the best way they can connect?
You can find me on LinkedIn or Instagram at @mrrickjordan. Both are great places to connect, and you’ll find links to the podcast there. Or just search my name on Google—you’ll find me there, and the podcast is usually right at the top of the page.
Awesome. Rick, thanks again. I appreciate your time.
Thanks, Dave. It was great to be on.
Thanks for listening to this episode of Wealth Strategy Secrets. If you’d like a free copy of the book, go to holisticwealthstrategy.com. If you’d like to learn more about upcoming opportunities at Pantheon, please visit pantheoninvest.com.