An exclusive conversation with JP Moses, co-owner and Director of Programs, Content & Culture at Awesomely, on the craft of teaching, the difference between high income and real wealth, and what it takes to build financial education that actually changes lives.
Hey Awesomely family. JP here.
You probably know me from the Daily Dose of Awesome emails, or from showing up alongside our Awesomely experts in our training programs. What you might not know is the longer story behind how I ended up here, what I actually do at the company, and what I’ve come to believe (the hard way, in some cases) about building real wealth versus just making good money.
Awesomely’s founder Patrick Riddle sat down with me recently and turned the tables, interviewing me the way I usually interview him. Here’s how that went.
How JP Moses Ended Up Co-Owning Awesomely
Awesomely: Let’s start at the beginning. How did you actually end up at Awesomely, and what’s the difference between the role you stepped into and the role you own today?
JP Moses: So, Patrick and I crossed paths on the internet sometime around 2008 or 2009. We were both active real estate investors and bloggers, both fascinated by this new world of internet marketing that was developing all around us at the time. He had a blog called MustKnowInvesting.com. Mine was REITips.com.
We happened to land in the same ecosystem at the same time, trying to build audiences and connect with our peers in the real estate investing world. There was a friendly competition called the Battle of the Blogs that pulled us into the same orbit by invitation, and that’s where our friendship started.
Fast forward to around 2012. Patrick had figured out that I was a more skilled content creator than he was at a base level, and as he was building out his information marketing game, he invited me to come work for him. I wasn’t interested in having a job. But I was open to a side hustle. So I started writing content and creating materials for his paid membership newsletter.
What I didn’t realize at the time was that I’d accidentally started a content marketing company. Like the Wizard of Oz guy behind the curtain. Patrick and another real estate investing guru at the time, Preston Ely, became my first two clients.
A few years in, Patrick came back and said he wanted more of me. We worked out a partnership and built a higher-level information marketing company together. We called it Awesome REI. AwesomeREI.com. It grew, we hired more people, we created more programs, all serving the same audience: real estate investors.
A few more years in, we realized we had a vision for a company that wasn’t just serving the real estate investing audience but a broader financial audience. That’s when we became a financial publishing company under the new name, Awesomely. And somewhere along the way, I realized I wasn’t only good at creating content that engages our target audiences. I was also good at building frameworks around other people’s expertise that accelerate the learning curve for our students. They can absorb things faster and more easily through my ability to act as a kind of interviewer or talk-show host.
So I went from writing all the blog posts and creating all the content myself, to hiring a team to do most of the doing under my mentorship. And I realized I also have a propensity for leading people in a way that aligns with the culture I want to build. Not just our culture internally, but the culture we reflect externally as a brand.
The whole concept of our mission to help people live awesomely (and the definition of what that even means) came from my own core value structure. So Awesomely has become a magnifier, at scale, of the things that drive me as a person.
Awesomely: You’ve described yourself before as more of a missionary than a visionary in your partnership with Patrick. What do you mean by that?
JP: Patrick is the visionary. He carries the long-term vision for the company and determines a lot of our trajectory. If he’s a visionary, I’d say I’m a missionary. I look at why we do what we do, and I come up with the most effective way to infuse everything we do with that mission and a clear set of core values that align with it.
I work hard not to be all things to all people. I work to be exactly who we’re convinced we need to be, amplify that, and attract the people who resonate with it. We’re not for everyone. But we’re absolutely for the people who get it.
The Role Between the Guru and the Student
Awesomely: You’ve called this the “host presenter” role. Why does this role exist, and what happens to a training program when it’s missing?
JP: Someone who’s a world-class topic expert isn’t always able to articulate what they have in a learnable, digestible way. The expertise is real. The ability to package it for someone trying to absorb it isn’t always there.
In the host-presenter role, I use a skill I’ve developed over the years: reflective listening, plus the ability to distill complex concepts into smaller, more digestible pieces. That helps our audiences understand at a deeper level what our expert is actually trying to teach them. I can also direct attention to bits and pieces of the expert’s story that I think are high value and worth knowing, but that might be uncomfortable or awkward for them to spotlight about themselves.
It’s just human to be hesitant to sing your own praises. As the host, I can freely showcase the impressive things our expert has built. I can use my own experience and conversation with them as a lens to help our students see more clearly what matters most about that expert’s journey.
Think about it like watching The Tonight Show. People who love watching Jimmy Fallon aren’t only there to see the guest. They want to see the guest through Jimmy. They want to be swept up in the wake of his observations and reactions. That’s an important role. It’s not always obvious to the audience, but it’s critical to giving them the experience they want.
Awesomely: Another way you’ve framed this is the “guide to the guru” metaphor. Unpack that one.
JP: I’m not the guru at the top of the mountain. Our expert is. Our audience is at the bottom of the mountain. They see the guru up there, and they want to get to the top, but they don’t know how.
I’m a little further up the mountain than they are. I’m within reach. I can see how they can get from base camp to the summit faster and easier, and I’m communicating with the guru at the same time. My job is to accelerate the learning, diffuse the complexity, and make the journey enjoyable instead of frustrating.
These aren’t skills most topic experts are even aware of, much less skilled in executing. So it’s a meaningful role from where I sit.
Awesomely: When you’re building a program with a subject-matter expert, what do you actually do to their content that they couldn’t do for themselves?
JP: I help our audience see more clearly the things that matter most. I create a framework that’s congruent with the outcomes we’re promising, but that also exposes the student to higher and broader levels of insight from our expert, so they’re aware of those things when they’re ready to ascend.
It’s a unique role, and a skill I’ve worked hard to craft.
Awesomely: What’s the difference between a financial education program that actually changes someone’s life and one that just sells well?
JP: A program that sells well promises a clear, compelling outcome. A program that changes someone’s life does that plus it actually delivers a customer journey that helps them achieve the promise, learn the thing, and figure out if it’s even the right thing for them in the first place.
That last piece is the one most program creators miss.
When we build a training program, I always tell our audience that this program exists to teach you exactly how to learn the thing and execute on it. But also, as an important part of the journey, we want to help you figure out if it’s even the right trajectory for you. Because not everything is right for everyone. You may get to the end of our time together and realize this isn’t really something you want to pursue long-term. That’s a kind of success too. Now you have real data to know whether you want to keep going or shift into something better suited to your circumstances and how you’re wired.
So in our financial training programs, we don’t create a soup-to-nuts, A-to-Z, whole-enchilada training on any specific topic. We intentionally ask: what’s the first speed-to-success training we can build to give people enough track with this to know if it’s even something they want to do? We always define a speed-to-success framework. Speed to first paycheck. Speed to first deal. Because if we can help you accelerate to your first financial win, that gives you real-life data. It proves you can do this thing. And at that point you should know whether you want to go all in.
That’s the kind of thing I wish I’d had access to early in my own career. Every time we make a program, I’m thinking about 25-year-ago JP, and asking what he would have needed and appreciated most.
What “Mission-Driven” Actually Means When Money’s on the Table
Awesomely: “Mission-driven” is one of the most overused phrases in business. What does it actually mean operationally at Awesomely, and what would we be doing differently if we weren’t mission-driven?
JP: When I hear about a company’s vision, that’s forward-thinking. It’s about trajectory. Where are we going and how do we get there. Mission to me is more about why are we doing this in the first place. Why are we even interested in accomplishing what we’re trying to accomplish.
For us, mission is about core values, and using a set of cohesive core values as a filter for all our operations and all our communication with the people we bring into our world. Years ago, when I sat with the big question of who are we and why do we do what we do, the words “live awesomely” were the first ingredients in my mind. I really sat with those words and tried to understand what they meant. To us, specifically. What’s the clear, compelling definition of “living awesomely” that we want to own?
What I landed on is this: to live awesomely is to always be leveling up. It’s looking for opportunities to be the best steward you can be of your time, your attention, your circumstances, your skills, and the possibilities in front of you. It’s stewardship and self-awareness, leaning into the opportunities you’re paying attention enough to notice.
So we crystallized it like this: always be leveling up. Shorten your learning curve. Create a life lived more easily, more awesomely, and more rewarding in meaningful ways. That can include leveling up your income (which is one of the most effective doorways people are willing to walk through), but it isn’t only about financial gain. It’s leveling up your mindset, your perspective, your self-awareness about who you are and who you want to be.
It’s harder to sell things like that as standalone products. So I weave all of it into our financial programs. I’m always trying to help people understand themselves better while they’re learning to level up financially.
If we weren’t mission-driven, I think we’d just be focused on what we can do to make more money that people are willing to spend. The mission lens makes the work meaningful and exhilarating to me. That’s why I wake up and do this every day at a high level instead of showing up to knock out tasks.
Awesomely: Walk me through a moment where the mission and the money pulled in opposite directions, and what you actually decided.
JP: This comes up more than people might expect.
We’ve had high-performing partners in our industry seek us out wanting to do deals with us. They’re not publishing partners in the traditional sense. They want access to our audience because we’ve gotten uniquely good at connecting with our customers and converting them into engaged students. These are some big names. People who could have moved real numbers for us.
We’ve declined many of them. We’ve walked away from high-caliber deals that were actively seeking us out, because they didn’t pass our sniff test as the right kind of people. The integrity of how they treat their customers didn’t measure up to ours.
Our customers trust our brand to elevate people whose values reflect or are symbiotic with ours. So who we partner with is a real decision filter for any deal. It costs us money. We’re okay with that. The trust is worth more than the deal.
What 20 Years of Real Estate Taught Me About Building Wealth
Awesomely: What’s the single hardest-won lesson from your real estate career that now shapes how you build educational programs?
JP: I touched on it earlier, but it really comes down to the value of creating a customer journey that accelerates someone to their first meaningful win.
25-year-ago JP would have found immense value in being given the chance to learn how to hit a first significant milestone fast, instead of being forced into a deep dive on everything all at once. Every training program I invested my own hard-earned dollars into early in my career over-delivered to the point of overwhelm.
I think that’s a common mistake when people create training programs. They feel like they have to teach as much as they can on a topic. They see comprehensiveness as a higher-value delivery to the end user. But what’s actually more valuable is helping someone size up early whether this is even right for them. So I want to give people enough to make real progress, achieve something meaningful as soon as possible, and use that as data to make the bigger call: do I go deeper, or move on?
That insight came from 20+ years of learning and educating myself as a wholesaler and real estate investor. Those are the things I wish I’d had in my own learning curve, so I carry them forward in everything we build through Awesomely.
Awesomely: Tell me about a deal or a mistake you’d never have understood the same way without losing money on it first.
JP: This takes me all the way back to the start of my real estate career.
After reading Rich Dad, Poor Dad and deciding I wanted to follow the buy-and-hold path, I started trying to learn about rental properties. My only measure of interest was the kind of financial success others had achieved through positive cash flow. But I didn’t know the business. Not really.
Early in my career, I met an experienced investor in the Memphis area who took me under his wing. He offered to sell me quality rental properties that would cash flow. I accepted his offer and eagerly let him guide me.
What I now realize is that he saw me as an easy yes for the properties he didn’t want to keep for himself. He was capable of finding good deals, but he kept the best ones (better areas, better numbers) for his own portfolio. The lower-quality stuff that still looked decent on paper, he had an eager buyer ready to scoop up. Me.
He did add some value to my learning curve. But what he was selling me were lower-quality rentals spread out all over town. They looked great on paper. I didn’t know until I lived through it that I was dealing with a tier of tenants that’s much more intensive to manage. More likely to default. More likely to destroy the property on their way out.
On top of that, he paired me with his property management company. And his property management company, without anything to compare it to at the time, turned out to be not a very good property management company. It just didn’t do an effective job of helping me manage my tenants or my properties.
A few years in, I discovered the world of wholesaling houses for quick cash. Which turned out to be a much better fit for my personality than buying and sitting on a rental for the long term. I could land a quality deal, find a cash buyer, flip it for a quick nickel instead of a slow dime, and move on.
There’s one month I’ll never forget. I closed my first sizable wholesale deal. I wholesaled a house for $10,000 more than I had it under contract for. Big win. Then I realized that same month I was going to have to spend all of that $10,000 to repair two vacant rentals in crappy parts of town that had been destroyed by tenants on their way out.
I had to use my most successful revenue month to just break even because of the financial drag of those rentals.
That month taught me a lesson I still go back to. The strategy itself matters less than whether the strategy fits the person executing it. Your personality. Your skills. Your circumstances. Books and courses showcase the exhilarating outcomes. What they don’t tell you is whether the work involved in getting there is something you’ll actually enjoy doing. The match between the work and the person doing the work matters more than most people realize.
That’s a lesson I think about every time we build a program.
From Awesome REI to Awesomely: Why the Brand Outgrew Real Estate
Awesomely: What did you see that made the rebrand from Awesome REI to Awesomely feel obvious?
JP: It wasn’t that real estate alone wasn’t enough. It was that we realized the mission and messaging we specialize in didn’t need to be limited to the real estate investing audience.
What we really specialize in is speaking to people who are seeking new income opportunities and a new life. People who need to level up financially from where they are. That just became obvious as we got more years into the company. The broader financial publishing model was a better fit for the engine we’d built and the outcomes we could generate for people. There was no reason to keep it artificially confined to real estate.
Awesomely: Crypto is now Awesomely’s growth vertical. What did you have to unlearn from 20+ years of real estate to take crypto seriously?
JP: Honestly, I don’t think “unlearn” is the right word. I’d say it was more about broadening our scope.
Patrick and I had both discovered Bitcoin years ago, independently of each other. A lot of what we’d learned about financial and economic principles organically through real estate elevated and amplified once we entered the world of Bitcoin and crypto. Then we hired Andy and Justin (two world-class players in the crypto space), and showcasing their expertise through the same lens and framework we’d built for our real estate audience became the obvious right next step.
There are nuances we keep discovering as we go. Advertising platforms like Facebook, Instagram, and YouTube aren’t nearly as friendly with crypto topic ads as they are with real estate. They’ve put it in a sketchier category, so it’s much harder to get paid traffic to operate at a functional level. We’ve had to rethink how we earn attention and reach the right people. The crypto audience also tends to skew a bit younger than our real estate investing audience, so we’ve adjusted our messaging accordingly.
But that’s not unlearning. That’s paying attention to what’s different, and using deductive reasoning and experimentation to refine how we operate.
Three Circles and Two Rules I Live By
Awesomely: You’ve got some rules of thumb you live by. Walk us through a few of them and where each one came from.
JP: There’s one I come back to over and over.
When people ask me what I do for a living, the truest answer isn’t a job title. What I do (and what I’ve always done if I look back at my whole career) doesn’t fit neatly into a job description. Looking back on my life, I realized that rather than pick a long-term trajectory and stay on it, I’ve always looked at what the right next step is based on three things: what I’m good at, what I enjoy doing, and where the opportunity is.
Think of those as three circles.
The first is what I’m naturally skilled at, based on my experience and how I’m hardwired. That’s a big one. The second is what I actually enjoy doing, which isn’t always the same thing as what I’m good at. If I genuinely enjoy the work, that matters. The third is where the real opportunity sits right now, in the world around me.
If I can find the sweet spot where those three circles overlap, that’s money. That’s what I do for a living. I look for whatever’s in proximity to any given moment where as many of those things are aligned as possible, and then I take that next step.
At various points that’s had me wholesaling houses. Bird-dogging deals. Blogging. Podcasting. Building content marketing companies I didn’t even realize I was building. Awesomely is the natural result of paying attention to those three circles and leaning into wherever as many of the boxes are checked as possible.
I share that framework with people all the time when we talk about career trajectory. It’s been one of the most useful filters I’ve ever stumbled into.
Awesomely: And the consumption-side rules?
JP: Two big ones.
The first is this: we borrow against assets to build wealth, not to spend more.
Debt isn’t good or bad. It’s a tool. The way you use debt, and how attentive you are to how you use it, determines whether it has a positive or negative net effect on your life and your goals. Earlier in my life I made the mistake of spending too much on credit cards to fund frivolous activities and toys. I learned the hard way that the cost of doing that very often far outweighs the short-term enjoyment.
As I got deeper into Bitcoin specifically, I absorbed at a much deeper level the value of having a long-term time horizon in the financial decisions I make today. So we have a rule: we’ll never borrow against our productive assets above our maximum loan-to-value threshold just to fund lifestyle inflation. But we’re willing (and even eager) to borrow against assets to build more wealth. That might mean a line of credit to fund a short-term real estate play before refinancing it long-term. Or borrowing against Bitcoin at a low-risk LTV to access tax-free dollars for a productive purpose. Debt’s moral quality is measured by the thoughtfulness of how it’s used, not by whether it exists.
The second rule is related: our wealth-building assets are not a lifestyle fund.
We’ll never let lifestyle consumption force us to sell real estate or Bitcoin or any productive asset. There’s an immense difference between someone who’s wealthy and has assets as the engine of their wealth, and someone who’s simply a high-income earner who has to keep producing more and more value just to keep the income flowing. One has an engine. The other is on a treadmill.
Using money to buy assets, and using the assets to fund lifestyle (carefully, thoughtfully, at low risk), is how the wealthy have lived for generations. That was a significant reframing of how I prioritize how I spend my money.
High Income Isn’t Wealth
Awesomely: What’s the most common thing people get wrong about building wealth that you wish you could fix in one conversation?
JP: Most people don’t have a clear understanding of the difference between creating wealth and building a high income. And not just the difference in outcome. The difference in process.
If I could go back in a DeLorean and talk to 25-year-ago JP, I’d tell him this: based on your preferences, your strengths, and the opportunity in front of you, you’re a much better fit for wholesaling houses for quick cash than you are for owning rental properties right now. You can and should be a high-income earner wholesaling houses. But that’s not all you should be.
While you’re generating all that cash wholesaling, you also need to be buying assets. The assets you should buy (back then, before Bitcoin existed) should have been real estate. But higher-quality properties in better parts of town, with higher-quality tenants, all in proximity to each other. Take your time. Find the right ones. Check as many boxes as you can. They’re easier to manage, more profitable in the real world, and over your career the wealth-building doesn’t come from the cash flow they generate. It comes from the asset price inflation that’s natural and inevitable as a result of money printing.
Wealth is built through assets almost exclusively, because of the broken economic system we live inside. The U.S. government and the Federal Reserve, in collaboration, have to keep inflating the money supply. As the money supply inflates, the dollar loses purchasing power. The natural byproduct of that is that the value of real assets goes up.
We shouldn’t have to use real estate as a high-octane savings account. But that’s the system we’re in. So the advice I’d give 25-year-ago JP is to use his ability to earn a high income wholesaling houses for quick cash, and use that income to build a portfolio of choice assets that will naturally appreciate. The wealth would build itself, for the rest of his life, through asset price inflation.
That’s the single biggest financial idea I wish I’d had earlier.
Awesomely: Last question. If someone reading this is on the fence about whether financial education is worth their time, what’s the honest case you’d make to them?
JP: Financial education isn’t optional. It’s the thing that determines the quality and trajectory of your entire life. The level to which you can make financially intelligent decisions shapes everything else.
Of all the categories of education a person could pursue, financial literacy is the one with the broadest, most compounding return. Most people will never get it from school. Most people won’t get it from their families. So the question isn’t whether you can afford to invest in your financial education. It’s whether you can afford not to.
That’s the whole reason Awesomely exists. We’re here to help people level up the most important area of their life through education that actually works.
To learn more about JP Moses and Awesomely’s programs, visit our About page or check out the Awesomely newsletter.