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In this lessons episode, explore how to build a scalable coaching business by selling expertise earned through real execution. Discover why starting with direct experience creates instant credibility in crowded markets. Understand how pre selling offers validates demand and accelerates cash flow. And uncover how refining positioning and funnels transforms one person hustle into an eight figure ecosystem. So the first version of that business, when you got a jail at a federal jail, you started, it was a social media marketing agency. Is that more or less correct, man?
B
So people that my like that know me well say I'm one of the greatest writers alive. And back then I would write for you for, for a hundred dollars a month, I would write five Facebook posts a day for you.
A
That's hard work. That's not easy work.
B
70 clients I had. It is, it is. And I, I had a spreadsheet, so I had like a system, blah, blah, blah, but, but, but yes, very hard work. I built this thing to 70 people. Again, no partners, no helpers, no investors, no bank, no advisors. I don't know what the I was doing. I just knew that I was on to something but I couldn't keep up with it. You know, it's like, but here's the cool part of that story is I got to learn different people's reactions and from 70 different social media accounts early on in the game, we're talking 2011, right? So I came out in 2012 and I said, man, you know, I didn't know how to scale a company, so I didn't know how to go and you know, maybe hire people or any of that shit, right? So I didn't know how that worked. So I just did everything myself. But then I thought, man, instead of doing it myself, how about now that I've got experience, I can just teach people how to do okay. And so that's when I got into the coaching side because that's obviously a more scalable. At least when you're one person, group coaching is more scalable than individual social media.
A
So okay, so when you're building this business, I find this really interesting because all the businesses you jump into are like super, super, they're super crowded, right? You're talking about social media management and marketing, you're talking about coaching. Like they're maybe not in 2011, but I mean like, like now, like there's.
B
A definitely not in 2011.
A
All right, so how do you. Okay, so you know, you put in the work, you, you know how to, you know how to kill it on social. You turn it into a coaching business. Even when you turn into a coaching business, there's probably a lot of competition with people that are maybe like traditional marketers that are trying to turn it, turn their own practice into a coaching business. But how do you differentiate yourself? How did you scale that up? And also, I want to talk, like, I want to talk numbers, like when you, when you start coaching, what is the product you sell? What's the service you sell? How much money can you make? What's the strategy to, to, you know, bring in leads, close them on a small ticket, high ticket. I find this whole thing so interesting. And also, like, I see the people that are doing it at like the highest levels, but you never see somebody that builds it from the ground up. You always see, well, you grant Cardone, like all the people that have been doing it for the past, like forever, and now you see where they're at. But to build a coaching, to build a coaching business from the ground up, offer true value, make true money, not bullshit your customers so that you're actually improving their lives in some capacity. Let's, let's break it all down because that's what I want to sort of unpack here. HubSpot Podcast Network is a success story partner. If you like success story, you are going to love some other great shows in the HubSpot Podcast Network. It is the audio destination for business professionals. One of my favorite is Business Made Simple. It's hosted by Donald Miller, an incredible friend, a great entrepreneur. Business Made simple takes the mystery out of growing your business. So if you're trying to figure out how to get to the next level, what Donald does is he gives you tactical steps that actually move the needle. And in your business, you can go listen to Business Made simple anywhere. You get your podcast. Business Made simple, part of the HubSpot Podcast Network.
B
So my very first rewire, which is my podcast, has about 4 million monthly listeners. My very first episode was sell on the level that you're at. And so that's what I did. And what I mean by that is in 2011, I was making 2010, 8, 9, 10. I'm making 20 to $30,000 a month, right. As a loan officer, which means you're doing about two or three million dollars on average in volume, which is five to 15 houses a month, depending on what state you live in, right? Just to give you some math. So here I am, a guy that's making almost a half a million dollars a year in a down economy. By the way, remember that Obama stepped in, Bush screwed up the economy, all the crap, right? It's not really presidents that do that. That's the narrative, right? And so Obama inherited a big mess. In other. In other words, that his administration was trying to straighten out in the mortgage business, where I'm working, right? And so not the easiest time to do business. I think I've always sold the hardest stuff, like mortgages in a downtime and social media management before anybody knew what the hell that was like. Now it's a crowded space. That's the, the, the objection. But back then it was like nobody heard of its Facebook. What? That was the, the objection, you know, so, but, so if I'm a person that sold $30,000 a month, I knew that I was one of the top producers, if not the top. I knew a top producer at my company, but I knew it wasn't the biggest companies out there. There were guys doing more than me. So I, I knew though, that I could teach people that were making five or $10,000 a month how I got to 30. So I go and I create a social media program. Because the social media accounts that I was running for those 70 accounts, they.
A
Were everything you knew, title companies.
B
Yeah, everything I knew, right? That's how I knew to post, right? So I stuck to what I knew. I didn't come from like mortgages and go, you know what? Like I screwed up. I came from mortgages and tried supplements and that didn't work, right? But when I went back to what I knew, okay, then the worked, right? So I knew that if I could get. Because see, what happened was when I got out of prison, I started posting on Facebook that I was top producer and then. Or. And that I was winning and all this stuff because I was hoping my ex wife that left me when I went to prison would see me still winning and then feel all stupid that she made that decision to leave me when I was down, right? But because of that, people started hitting me up going, hey man, can you do my mortgage? And I'm like, I'm on to something, you know, and, and again, this is in the now that's like common sense. But again, this is in the early days of all this. So I'm like, I'm really on to something here. So I start teaching, I make an ad. This is the event that I go to in Vegas. I make an ad to loan officer. It says if you're a loan officer and you're not doing at least $2 million a month in mortgage volume, fill out this application. Let's get on the phone and let me show you How I consistently do $30,000 a month in mortgage commissions with no team, no assistant, no personal processor, and I don't even know the name of the underwriter. Fill out the application below and we'll get on a phone call. So what happened was it was a YouTube video on a Wufu. On a Wufu, like which is a survey monkey type of thing. And then that transpired into my own. I still have all this. Then that transpired and took place into my calendar link.
A
And that's like the, that's like the first funnel. That's like the funnel right there. That's the first funnel. Gotcha.
B
That's it. That's it. And so a guy named A.J. roberts helped me construct that at that event in Vegas. He sat to the side and, and showed me how to do that. Within about 20 minutes we had, I already had the video because I just recorded on my phone. It was like super easy to do that even back then. So then because of that I got all these calls. And so I'm selling a product that's $2,000 for six weeks, six week training, $2,000. Okay, here's what most people do, okay? They say I'm going to go and create a digital product. And so they go and they spend time creating this digital product and then they go to sell it and then nobody buys the. And they wasted all their time building it, right? They wasted their time building something that nobody wants. So what I did was I made sure everybody wanted. So I pre sold it as a six week boot camp and then I recorded each of the six weeks and then turned those into a product and then sold a digital product.
A
You didn't waste any time at all.
B
I didn't have no damn money. You know what I'm saying? Like I didn't have the money to waste time. Like I didn't have a bank partnership like I keep saying. So like I do what your audience. I had to hustle. And so, so but what the, the way I priced it was if you do one loan, the average loan in America at the time was about $203,000. And if you're a loan officer, you typically take home 1%, maybe more, but on average 1% of that loan amount and is what you're actually putting in your pocket. It's not the, what the company gets and everything else, but it's what you actually pocket is 1% of the loan, right? And so if you have a $203,000 loan, then you're getting $2,000. So my whole Pitch on the phone call was like, look bro, for sure we can get at least one more loan over the course of six months because or six weeks from what I'm going to teach you, like surely one more loan will come in to pay for this. So literally my prospect has the belief that like, I mean I can't really lose if I one, one deal that kind of pays for itself. It makes it kind of a no brainer because, because again back then they're like, I don't know about this Facebook, bro. And now you want $2,000. But I'm like one deal. You close one deal man, and you got money. But you close two deals, you're in the black, you're in the, you're in profit city. You know what I mean? What happens if you coach two deals a month and then four deals a month and then those give you referrals at least the five deals a month. This is something that's going to carry you for the rest of your life. So nobody would tell me no unless they didn't have two grand. But check this out. I got to a point where I couldn't keep up with the calls. So I've got this digital product. I'm the only sales guy, I'm the only marketer. I'm making the funnel, making the video, editing the video, doing I don't got no help, right. And so, and that at this point I have money. I just not smart enough to hire help. I didn't know how all that worked. I know now, but I just, I didn't have mentors and to teach me. So I'm doing all this myself and, but what happens is I get to a point where I'm, I'm making a whole bunch of calls and, and maybe only, you know, 50, 70%, 70% of the people probably can't buy because not a lot of people back then had $2,000.
A
Especially mortgage, especially mortgage brokers in the recession, like that's not a good time for them.
B
My competitor at the time, mortgage marketing animals their product was 47 bucks a month. And I'm telling them I want two grand. I was the most, I was the Louis Vuitton purse of the mortgage industry coaches at that time. Right. And so, but what happens? So about 70 of the people wouldn't do it. So with 30 still a big ass closing ratio for most people, not so much then make me happy now. But back then it is what it is. But, but what happens from that is I couldn't keep up. Now I'm wasting 70 of my time with people who didn't have money. Right. That was their objection. Wasn't. I don't believe in it. They clearly, they filled out the app because they wanted it. They just found out it was too much money for what they had available in their credit card lines or whatever. So what I did was I went back to the video and I changed the offer from if you're a loan officer doing 2 million or less to if you're a loan officer who's closing at least $2 million a month, I want to help you get to five or more as fast as possible. So at that point, it takes all the people who. Because less than 2 million can be zero. Right. But a minimum of 2 million lets me know at least you're making about 20 grand a month. Right. And on a W2, so you at least got $11,000 or so. Take home that you're coming in every single month. Right. So allowed me to go. And then all of a sudden I'm closing about 70% of those conversations because those guys, two grand's nothing. Oh, yeah, I'll give it a shot. Whatever. It's tax deductible. And so like, eventually there's only 300,000 loan officers in America and I sold products to 20 something, thousand of them. So eventually I kind of ran through that marketplace pretty good, right. And I got bored. And so I. And I realized that I had a bigger gift than just social media to loan officers at this point. I'm running a full blown company with employees and I've got multiple companies and investments and all this stuff going. You know, a few years ago and I decided I wanted to just create a, like, not just products and not just coaching, but I wanted to create a, a network and a movement of people. And so I created this, this Apex program where, you know, we have basically three tiers in it. But it's evolved beyond me. It's not the Ryan Stuman show. It's not the, you know, come being Ryan Stewman's mastermind. It's like, come be a part of something where people represent what winning looks like. Come be a part of something where it's some of the best of the best in their respective industries where you can get to learn from no network. And I get to put unknown names that are brilliant with huge companies and on stages to speak that wouldn't Normally get the FaceTime and stuff. And it's. It, man. It's just, it's evolved into something now that's got 2,00,0 active members. And you know we are doing more money than I'm really comfortable saying. But if I said that the big if I if if just know that we are doing well. Well like well the eight figures a year this year we already well the into eight figures a year this year we are well deep into 8 figures this year with only 2 sales guys.
A
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Episode: Lessons - The Ex-Con Who Built an Empire | Ryan Stewman - Sales Coaching Mogul
Date: December 29, 2025
Host: Scott D. Clary
Guest: Ryan Stewman
This episode of the Success Story podcast explores the remarkable journey of Ryan Stewman, a former convict who transformed his life by building a multi-million dollar sales coaching and business empire. Stewman and Clary dissect the foundational steps of creating a scalable coaching business, emphasizing the power of leveraging personal expertise, validating demand before building products, and evolving from a solo operator to the founder of a thriving entrepreneurial network.
On scrappiness and early struggles:
"I didn't have no damn money. You know what I'm saying? Like, I didn't have the money to waste time. [...] I had to hustle." — Ryan Stewman (07:51)
On the psychology of pricing:
"My whole pitch on the phone call was, like...for sure we can get at least one more loan over the course of six weeks from what I’m going to teach you..." — Ryan Stewman (08:25)
On overcoming the solo founder bottleneck:
"I'm the only sales guy, I'm the only marketer, I'm making the funnel, making the video, editing the video... I didn't have mentors." — Ryan Stewman (08:48)
On accelerating through niche focus:
"Eventually, there's only 300,000 loan officers in America—and I sold products to 20-something thousand of them. So eventually, I kind of ran through that marketplace pretty good, right? And I got bored." — Ryan Stewman (11:18)
Ryan Stewman's journey showcases the transformational power of leveraging lived experience, starting lean, validating market demand, and consistently refining both offer and audience. His candid recounting of operational mistakes, pricing psychology, and ultimate shift from solopreneurship to building a sustainable, scalable ecosystem offers real, actionable insight for anyone interested in the coaching or expert business space.
If you want more in-depth strategies or to hear the full conversation, check out the episode on the Success Story Podcast.