Interview with Patrick Riddle: Founder of Awesomely

Real Estate Investing20 min read

An exclusive interview with the Founder of Awesomely.

JP Moses
JP Moses

Hey Awesomely family, founder Patrick Riddle here with some words today. You might know of me from Awesomely and the Daily Dose of Awesome emails I get to pen sometimes, and others might know of me from my real estate investing adventures. 

So, I thought it might be helpful to share some more info about my entrepreneurial journey, backstory, and experience, with some helpful advice thrown in, too, so y’all can perhaps relate and even learn a few things.

Take a looksie at this insightful convo I had with Awesomely’s president, JP Moses.

Let’s do this…

JP Moses, Awesomely President: What was the starting point of your entrepreneurial journey — how did it all begin?

Patrick Riddle, Awesomely Founder: So, growing up, I always kind of knew that I was going to do something different than my parents. I saw them going to work every day. My mom’s a schoolteacher, my dad worked in healthcare for a long, long time, wearing a suit every day. And I was like, “Man, whatever I do, I’m not doing that!” 

But I didn’t really know what. Until college. But it’s not what you think…

My big entrepreneurial career kicked off one summer when a couple friends and I were living in Charleston, South Carolina, on college break. We ended up meeting a guy in his late 20s who owned a few rental properties. He told one of my buddies, Jonathan, about appreciation and some of the benefits of real estate.

Then, we had the bright idea to go to Barnes and Noble — yes, there were plenty of those still around back then — and we bought a couple books. One of them was a book on lease options by Peter Conti and David Finkel: “Making Big Money in Real Estate Without Tenants, Banks, or Rehab Projects.”

So finding ourselves in unchartered territory — a bookstore — actually led to us hearing about a free one-day seminar. A handful of experts spoke, and one of them was Lou Brown. When he was answering questions, we realized that’s the guy we want to learn from because he seemed next level with his knowledge and experience. 

After that, we connected with Lou’s company and signed up for his 5-day bootcamp seminar. (BTW, this was during college now… we all skipped a week and went to Atlanta.) I’ll just say our minds were blown.

By the end of that big seminar, one of my buddies decided he was quitting school and going all in. And it didn’t take much twisting of our arms for me and our other pal, Dusty, to make the same decision too. 

And it was around the time of that seminar when we actually closed on our first property.

We went the “traditional” route — one of our friends had a relationship with an agent and had been looking at properties. He had decent enough credit, and we had a small amount of funds to put down on a house. 

We closed on our first property in November 2002. 

We were all in. 

That December, I waited till after Christmas to tell my parents that I wasn’t going back to school, and my buddies and I were moving to Charleston to go into business.

And that’s what we did. That was the kickoff.

Awesomely: Wow. In retrospect, was there something about real estate investing specifically that resonated the most with you, as one of the possible ways to start your entrepreneurial journey? Or do you think it was just the thing that was in front of your face, the most obvious starting place because it’s a big opportunity, and the people involved at the time?

Patrick Riddle: Well, before I told him that I was quitting school, I remember sitting in the den reading “Rich Dad, Poor Dad,” and thinking, this is like the gospel. But, as many of you, if not most of y’all reading this already know, some real estate education often leads to other books on business. Y’all probably heard this too, the real estate path is how most of the wealthiest people in the world became so wealthy. 

So, we thought, if we create a business that’s all about investing in real estate, that’s the B and the I quadrants from “Rich Dad, Poor Dad,” that must be the best. 

See, before we discovered real estate, which was the first endeavor we actually jumped in and did, my friends and I had tried coming up with random ideas of how we could make money. We considered buying a Golden Tee machine, it’s an arcade game for golf, and putting it in my fraternity hall. I mean, we had all kinds of harebrained random ideas for how to make money. 

But once we came across real estate, we realized that we could do it without money or credit. Yep, we actually believed the outrageous claims in books made, which, as you know, are true in many instances, especially with creative real estate.

Awesomely: Ok, at the end of all of Awesomely’s intro kickstart videos in our training programs we create with REI partners, we always ask the same important question: “What’s your why?” Now, as you know Patrick, what we’re asking is why you’ve chosen to be an entrepreneur. And, the answer can’t be because of the money. The money is the thing that gets you to the why. So, what is the fuel that makes you want to continue being an entrepreneur who’s committed to the journey that you’re on?

Patrick Riddle: So, I’ll admit, the money aspects of REI were interesting. But as soon as I started learning about real estate and started buying houses and becoming successful, I just wanted to spew what I was learning to others. I feel like I am a teacher at heart. Like I said, my mom’s a schoolteacher, my dad, even taught some graduate level courses at the University of South Carolina on the side. 

And something inside me as a teacher erupted just a year into my investing career. So, we started teaching and training others locally on our door-knocking strategies and campaigns. We had a field of bird dogs out there knocking on doors for us. And it was natural for me to want to teach. 

When I shifted into the education business, I began getting amazing emails from folks we’ve helped educate. I love them! And it’s not just from somebody who closes a deal and makes money — it’s hearing from people who say, “Because of you, Patrick Riddle, I did this thing that I didn’t ever believe I could do… I actually called a seller. I’ve been scared to do that and haven’t called anyone for 2 years, even though I’ve been reading books and going to seminars.”

It’s those breakthroughs along the way — professionally and personally — that do it for me: hearing how something I shared helped them overcome some obstacle or achieve some great thing. 

And all that led to the business that we’re in today. We’ve built Awesomely around providing the best of the best, good step-by-step, comprehensive, actionable education that people can take and change their life.

Awesomely: So is it fair to say that while making a profit is obviously a critical piece of the puzzle, another critical part of your “why” is making a difference in what you’re doing to make a lot of money? It’s making a difference in somebody’s life, whether that’s providing them with a better home or providing them with a better income stream or just something that moves the needle in a positive way for their life.

Patrick Riddle: Yeah, providing people an opportunity. Here’s an example: We put someone in a rent-to-own property, and we helped them qualify for a mortgage, and they bought it from us 2 years later. And I was amazed at the time, thinking, “Wow, we really changed things for these people. We did this deal, gave them an opportunity, and now they’re homeowners.” 

Those situations are so fulfilling. But there’s more…

We also improve neighborhoods, which helps all the people in the area. Say there’s a dirty old vacant, abandoned pile of crap next to your house and we come in and make it really nice. Seeing the transitions of houses before and after and enhancing the community is also super fulfilling.

All that’s great, but my big “why” always comes back to teaching and sharing education with others and seeing how it’s impacted them in a positive way. That gets me excited.

Awesomely: Question related to something you said earlier. You mentioned a few resources that you found insightful and valuable early in your entrepreneurial career: “Rich Dad,” Conti, Lou Brown. Any other books or resources that you found particularly relevant and helpful?

Patrick Riddle:Think and Grow Rich,” Napoleon Hill’s classic. And classic personal development books from Tony Robbins, like “Unlimited Power.” I mean, I basically read them all in my ‘20s in the 2000s. One of the big personal development books that I got a ton from was Brian Tracy’s “Maximum Achievement.”

Awesomely: Can you think of an unexpected challenge that you encountered in your entrepreneurial career? 

Patrick Riddle: Yeah, I don’t think you realize how hard going into entrepreneurship can be. Not only are you having to push through your own mental barriers, but sometimes working in partnership scenarios can be difficult. I mean, buying a house is one thing, but then running a business is a whole other thing. There’s a lot to learn. 

As you get started, the first thing to focus on is bringing in some sales, some kind of revenue. And as you encounter problems and issues, you just tackle one thing at a time. 

Something that was tough early on was my business relationship with friends. I got started with two friends. After our first year, one of them parted ways abruptly. Now, we didn’t let that affect friendship, but it changes the dynamics — we had to absorb the responsibilities and position that that person was executing for us.

Having said that, you know, you should expect challenges and hurdles and curveballs. What’s important is how you respond to all those things.

Oh, rather fitting, another seminal book for me is “How to Win Friends and Influence People,” the Dale Carnegie classic. I’m telling you, the world would be a better place if everybody read and paid attention to what he teaches in that book.

Awesomely: Let’s talk about what you’ve learned from the School of Hard Knocks throughout your success journey. Of course, we learn a lot from our wins… as well as our fails. 

Patrick Riddle: The biggest “Hard Knock” early in my entrepreneurial career was when 2008 hit. The huge market change pretty much put us in a position where our real estate business model was broken. 2008 revealed that the business model we were executing no longer worked. 

One big lesson during that crash was cash flow over equity — equity can disappear overnight, in essence. The lesson I learned was to own something for cash flow purposes, not for equity. If the value of a property changes, and then you have to sell, but can’t sell it for what you owe, that’s a tough position to be in. 

But if you’re in a great cash flow scenario, it doesn’t matter whether the value goes up and down necessarily, because even if it’s worth less than what you owe, you’re cash flowing positively on it, so you can withstand some tough times. 

So, being an entrepreneur, I learned in one of the books about the idea of falling on the sword at times. You’re gonna get in disagreements; people remember things differently, and sometimes it’s valuable to take the hit yourself in certain scenarios to preserve a relationship instead of it ending a relationship. 

See, a lot of times people will choose to be right over being rich. They’ll prefer to be right than preserve a relationship that could add value and revenue and money for years to come. So at times, when you’re butting heads and disagreeing with someone, be willing to take the hit, be ok with it, and move forward and preserve the relationship, rather than let something sour over money. 

Awesomely: Let’s talk about our company. Briefly summarize when and why you decided to start it.

Patrick Riddle: Well, as I mentioned, really enjoy teaching and knew that at some point I wanted to start an education business. So I started a blog called “Must Know Investing” in 2008. And after about 6 months of posting consistently on the blog, I started reaching out to other people in the niche that ran other kinds of small- to medium-sized websites and blogs. 

The first two people in the space that I reached out to who emailed me back were Trevor Mauch, an investor, entrepreneur, and author and JP Moses, who’s now Director of Awesome at Awesomely.  So when I reached to possible connections, I’d share my professional background, show my website, and ask If I could share content with their audience and provide any kind of value to their site. I actually still have my original email exchange with JP.

Anyway, so I connected with Trevor — he had a website and an audience, with a growing list, but he didn’t have much experience in real estate. He had a couple properties, but he was more of a marketer and web guy. 

So when he and I connected, with my expertise in experience in real estate, we decided to do a content webinar that he promoted to his list to get the people there. I showed up to teach the content. And in my investment business, I was always really good at recruiting private money. So that was the topic that I taught about. There were about 100 people on the webinar, and we got some good feedback. We did one more about a month later, and then people started asking for more. 

So we decided to create a 6-week private money training program. It was live training; we sold about 20 people into it. And I was preparing the content for each upcoming week. Once we completed this 6-week training program, we took all the recordings that we had created and wrote a whole big home study course. We launched that first home study course called “Private Money Blueprint” in May 2009. We sold 1 thing together, that course, and it went well. And that’s when my company was incorporated. I didn’t seek out to start a company with Trevor, it just happened naturally as we did a couple of those webinars. 

Awesomely: Fast-forward and briefly talk about the transition from Private Money Blueprint to Awesome REI.

Patrick Riddle: So Trevor and I were the founders/owners of the company — Trevor was running the company and handling all the marketing, and I came in as the content and sales guy. For the first few years that we worked together, we created a variety of courses, products, and services for real estate investors. It was all geared around the topic of recruiting private money. Eventually, Trevor and I parted ways, on good terms.

Then when JP and I connected, we talked about a vision for the company, offering products on a lot of different topics. It was at that point that we knew we wanted to rebrand the company to a name that made more sense than the original course we’d created, Private Money Blueprint. So that’s when we rebranded to Awesome REI in 2015.

Awesomely: How is Awesomely different from Awesome REI?

Patrick Riddle: Awesome REI was creating both courses and software and even some coaching, all specifically related to real estate investing. Then in 2019, we focused the business Awesome REI on doing 1 thing, which was creating our high-quality, low-cost educational courses for real estate investors. And that’s been our focus for the past few years. 

The shift from Awesome REI to Awesomely came because we began expanding to offer courses in other financial opportunities, not just real estate investing. So in the near future, we’ll have courses on different stock market stock opportunities, real estate, other business opportunities, cryptocurrency, and any kind of financial income strategy opportunities.

Awesomely: So to summarize in a way, it’s fair to say that it made all the sense in the world to start publishing, training, and content creation to help other people like you — who were struggling in the real estate investing — in their real estate investing journey, because you can pull from the wealth of experiences, wins, and losses to help them accelerate in their own success. And in that process, you realized you had something really special that could help other people in their success journey who are trying to achieve it through some other channel besides real estate investing. We seem to be really good at what we’re doing, and we think we can do it at a higher level and help more people, so it made sense to blossom and grow beyond.

Patrick Riddle: Yeah, we saw the opportunity where we could have a much bigger impact. We believe the specific way that we create our courses and sell them enables us to have success with other financial opportunities that will also appeal to more people.

Awesomely: Let’s talk about the training aspect: How important is this concept of training within your success journey, either as a real estate investor or a crypto investor or just an entrepreneur in general, what role does training have? And is it a make or break in your success journey to have the kind of training that create to help people?

Patrick Riddle: It’s a fast-forward button, and sometimes it can help you skip over mistakes that you might make on your own if you try to do it yourself. Sure, you can go online and find articles and videos on various things and you can take action. Some people could do it themselves and have wild success. 

There are opportunities, though, to take a much faster path to success that’s easier, less cumbersome, and with fewer bruises along the way by leveraging the knowledge and experience of somebody who’s been there before you. There are a lot of pitfalls along the way when going after different opportunities, like the trainings we provide, that people don’t know. 

Awesomely: Something that comes to mind for me that’s related to that is that I think a common objection people have to investing their time or their money into a training is you can find anything you want for free on the internet on YouTube University. 

Patrick Riddle: That is true, but it’s also kind of like the difference between putting together a puzzle with the box of the outcome and all the pieces contained in one box versus all the pieces to all the puzzles all over the place — you can still put together that puzzle successfully, but it’s going to take you a lot longer. There’s going to be a lot more trial and error, a lot more failure, and you you’re much more likely to give up before you even get the corner pieces, much less finish the puzzle. 

Awesomely: But when you go through a training program with a thought leader who is high success and high trust, who has the right stuff, you can accelerate your progress in mirroring their results. It’s like getting a puzzle that not only has all the pieces in the box, not only does it have the picture of the puzzle, but you have a blueprint of where pieces are and what you put together first, then what comes second and so on. It’s like a map to putting the puzzle together faster than you ever could. Does that resonate with you or would you say it differently?

Patrick Riddle: Yeah, I like that. So, there’s the do-it-yourself model, the do-it-with-someone-else way, and the done-for-you approach. When you’re leveraging a course like Awesomely creates, it’s “done with us.” We’re there for you, we’re showing you, step by step, what’s worked for someone else. We’re explaining, the common obstacles, pitfalls, things you want to make sure to avoid, and where to focus your time and the different resources, all packaged together. 

An advantage that we create is that everything’s step by step, and it’s all contained for you, all in one program. Plus, you also get Awesomely’ s superb customer support to answer questions and help point you to additional resources when needed.

Awesomely: Tell me about the culture that you’ve created at Awesomely, and how it’s positively influenced our team and people’s lives?

Patrick Riddle: We have a pretty laid-back culture, yet one way to get things done that’s part of our culture is how we all communicate with each other with a certain level of respect. And it’s interesting because our company is completely virtual. We’re 100% remote, but we’ve still been able to develop and instill a unique and friendly, fun, positive, and unique culture.

I think a lot of people can feel our culture when they reach out to our front lines of support staff and especially when we all are together in person and on our company-wide virtual meetings — it’s the way that everyone respects people and the way we communicate with each other as a team. Fortunately, there isn’t infighting or political games in Awesomely. We’re all here for one purpose, and everybody’s truly on board for that.

Awesomely: Do you think it’s a meaningful part of our Awesomely company that we deliberately position ourselves not as the guru on the mountaintop, but as the guide to the guru? We position ourselves as the advocate who can help accelerate people’s path from where they are to where the expert that they’re pursuing is. Do you think that that level of relatability is part of an important aspect of our humanity?

Patrick Riddle: Yeah, and I’ve been through a lot of educational courses. If I want to learn something new, I’m all about the shortcut, the fast-forward button.

And having been through a lot of educational courses and created them myself, before JP took over our product department, when you have an expert speaking to you — one person through hours of training — there’s a difference between that dynamic and the dynamic of all of our trainings now, which is a host presenter setup. I believe the host presenter setup — and especially someone who’s really good at hosting — presents an opportunity for clarification, reinforcement, and all the things that are added that really make for more consumable training, which really helps people watching to better understand what we’re teaching.

Our role in creating a training program is to do what we can to make a person’s success journey as painless, fast, and easy as we can.

Awesomely: If you had a DeLorean and could go back in time to talk to young Patrick Riddle, knowing what you know now, what advice would 40-something-year-old Patrick Riddle give 20-something-year-old Patrick Riddle? (Besides getting a turkey frier earlier!)

Patrick Riddle: I’d say, like many entrepreneurs, you’re going to have many ups and downs, so realize that no matter how down things are, you’re going to make it and and everything will be ok.

Awesomely: What advice would you give to people who are looking to kick-start their entrepreneurial journey — what can they do to get off the ground faster, sooner, easier? 

Patrick Riddle: Well, some advice is to expect obstacles, challenges, and brick walls. If you really want to be successful, commit to getting back up no matter how many times you get knocked down.

I think a lot of entrepreneurs make a mistake of going into a certain business or field, and they try, try, try, and when they don’t see success, they move on to something else and continue that pattern.

It’s important to commit to something, see it through, and not letting obstacles get in the way. Resilience. If you want the easy way out, then don’t be an entrepreneur. Go get a job. It’s a lot easier to get a job to earn income, than to be an entrepreneur. But, there’s a lot of benefits to being an entrepreneur.

Awesomely: Last question. What decision filters should you use when choosing the right program?

Patrick Riddle: While it is a personal question, Awesomely specializes in creating educational courses for people who are new to a topic or niche and trying to find their place in this world. We’re there to help them find it.

So, it depends. If someone’s looking to earn extra money, that’s one thing. If they’re looking to grow existing money, that’s another thing, and I would point them to a different type of course, depending on where people are at personally and financially, to choose the business model that fits their lifestyle. 

A lot of times people don’t think about the lifestyle component and end up building a business where they hate what they do. I would say choose. For me, I choose lifestyle over money. What I mean is, if there’s a strategy in which I could maybe make more money, but it takes away from my lifestyle, I’m less likely, personally, to do that. 

And there’s risk tolerance. If there’s an amount of money, a financial commitment, I’d suggest starting with something that’s lower risk: wholesaling rather than fixing & flipping, for sure. Do some wholesale deals first, build up a little capital, and de-risk things a little bit before trying a more advanced strategy.


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