In this no-nonsense episode, Sheldon Wolf, Founder of Intellitary Real Estate & Mortgage Referral Network, shares why “follow your passion” is dangerous advice and how to build businesses designed to profit from day one. If you’re thinking about starting a business but worried you’ll turn a hobby into a money pit, you won’t want to miss it.
You will discover:
– What the hidden costs of customer acquisition do to true profitability
– Why following your passion alone often leads to starting the wrong business
– How to build a business backwards from monetization instead of from the idea
Episode Transcript
Scott Ritzheimer
Hello, hello, and welcome, welcome once again to the Start Scale and Succeed podcast-the only podcast that grows with you through all seven levels of your journey as a founder. I’m your host Scott Ritzheimer, and there is some very, very bad advice that we in the coaching profession like to give. That advice is follow your passions, and especially for those who are thinking about starting a business, who are thinking about, in some sense, risking it all to go in and try their hand at the entrepreneurial game, that could be a disaster waiting to happen. If you’re not, if you’re not careful, that could be one of the fastest ways to end up starting the wrong business altogether. Well, here today is our guest Sheldon the Wolf Wolf, who is a serial entrepreneur, investor, and business architect with more than 30 years of experience in real estate, finance, lending, and technology. He spent his career identifying broken business models and redesigning them from the ground up.
Today, he is the founder and CEO of IntelliTary, an AI-powered unbrokerage, strategically engineered backward to scale rapidly, generate substantial recurring revenue, and maximize enterprise value. Sheldon believes that the biggest opportunities aren’t found by improving existing industries; they’re created by seeing what everyone else misses in challenging the assumptions that others accept as fact. Andy’s here with us today, Sheldon. Excited to have you. I’m really excited about this conversation because a lot of what people think about in starting businesses is is either kind of problematic or really bad and boring to start with. So it’s hard enough as it is to start your own thing. How do we make sure we’re actually starting one that’s worth starting?
Sheldon Wolf
Well, see what’s interesting about me is I wear two hats. One, I’m a founder. Two, I’m an investor. So when I build businesses, I always build them backwards. Backwards is the best way to build a business because you’re starting from the monetization. You’re starting from where it becomes profitable. A lot of people start from this crazy idea they got while sitting around eating fries at a diner on a Sunday afternoon. Out comes the napkin. Out comes the pen. And sometimes these things are great. Sometimes people take their hobbies and say, “Oh, if I can make a living doing this, that’s sometimes the wrong approach. If it’s not going to make you money, then keep it a hobby. So I build things backwards. I always design them to monetize, and I’ve built a specialty of turning problems into profit because I see that far too many times people do jump into that business that really should be a hobby, and they go, “Well, it’s not monetizing, or it’s not bringing in the revenue, or it’s bringing the revenue, but there’s no profit. You know, it’s that kind of thing that I specialize in.
Scott Ritzheimer
Yeah, so good. So I want to distinguish between this because I really love the language of a business or a hobby. So tell tell me what the difference is, because and correct me if I’m wrong, but I kind of think of like I love playing music. I love playing music. If I had to make a living paying music, I think it would take all the joy out of it. So, am I onto something like what’s the difference between a hobby and a business? How do I know the difference?
Sheldon Wolf
Well, you’re 100% correct right there. I love cooking. People told me for years and years and years, you should you should open a restaurant. You should forget it. That’d be the last thing I’d ever want to do. Even even if I thought for one second that I should, all I’d have to do is look at the financials from most restaurants, and I’d say, run, run, do not do that. There are successful restaurants, but really, at the end of the day, for every one really successful restaurant making lots of money, there’s there’s nine of them that aren’t, and you could you could take that to a lot of businesses, especially in this day and age of all these techy entrepreneurs out there, and and a lot of the stuff that’s being designed, you know, I see the wall coming. I see the wall miles before it gets here, and I just see far too many things that are flimsy, and they just haven’t they haven’t been designed to make money, or or as a hobby, you feel bad because you don’t want to profit from other people doing what you’re doing. You know, it’s this guilt that people have. A lot of times, people are their own worst enemy, and and not everybody should be in business. Not everybody should be an entrepreneur.
Scott Ritzheimer
Yeah. So let’s talk about that because you’re you’re speaking the language that I think has gone through folks’ heads, and there is this, especially the things that we are most passionate about. There is this really difficult tension of like, how how do I price it? Is it worth it? Should I charge for it? What if somebody doesn’t pay me? Should I pursue it? Those things seem to get so much harder when. We’re passionate about whatever it is that we do, but on the flip side of that, if if you don’t care at all about what you’re working on, does that work either?
Sheldon Wolf
You have to love what you do. That’s the first thing I’d say. No matter what you do, it has to be something you love because you’re kind of getting married to your business in an obscure way. It becomes your partner, so to speak, and you become its partner. It’s it’s an entity relationship, but the the fact is, if you hate going in every day, doing what you’re doing, it becomes tiresome. And you know, it’s funny is even some successful successful businesses, when you hate doing that, even even the even the glisten of the gold wears off real quick. You gotta love for for longevity’s sake. If you want to keep this business up and running for long term, and if you don’t, well then don’t do it unless that is your goals a long term business. But notwithstanding, you gotta love it. I love like to me doing deals every day and business every day and problem solving. To me, it’s like going in and doing different puzzles, playing different games. I mean, people ask me all the time what makes me different. I treat business as if it’s like a sport, and I don’t step in the ring just to step in the ring. I step in the ring to win. Absolutely, everything I do is revolving around winning each and every company I build out. Every time someone says, “Hey, I’ve got this problem with my company, help, it’s me stepping in the ring. And if you don’t have that psychology where you’re there to win, like I said, that’s that’s half of it is what goes on in your own mind.
Scott Ritzheimer
Yeah, it’s fascinating that we’re having this conversation because just this weekend I was actually thinking about it quite a lot. I was at a cross country race, and cross country races for anyone who’s not been to them are like these giant affairs with with 1000s of children that are running. You know, it’s like when I played soccer as a kid, punishment was running. Right, is what happened when you did something wrong? These these kids have all voluntarily chosen to run miles and miles on a Saturday morning at six a.m. It’s insane, and one of the things I recognize, especially as watching some of the faster runners and knowing the work that went into that, they didn’t just show up on Saturday morning and and win. They ran mile after mile after mile, out of the limelight, in obscurity, on their own, just putting in the time and to to really win, you can’t just love to win. I think you have to love what you do as well, but you you have to love to win as well, right? It really is both, and and I hear that in what you’re saying, and so when when we get into this game, right? We we love what we do, and we love to win at doing it. How do we take that and kind of drill that down a little bit closer to s ay, what’s the best opportunity in that kind of Venn diagram?
Sheldon Wolf
Well, a lot of it is vision. A lot of it is creation. It’s all these other ingredients. So one of the first things I said is I build my companies backwards. I want to see how profits. So a good example is I had a conversation with somebody this morning who’s been bugging me because she wants to do business with me and she wants me to fix this thing she’s created. It’s it’s in the credit business. It’s a fintech program she’s built that involves credit scores and whatnot. But the problem that she has, and I just looked it. I didn’t need to diagnose it and ripit and shred it. But it’s one of those things that she has to pay $8 to get the credit report, something like that, and then she has to resell it to somebody for $12 because there’s only so much someone’s going to pay her for whatever the service is. So essentially, she’s making $4 at a at a shop. But I can tell without even touching anything. This is just where my experience comes in. I can tell you right now the actual cost of a customer acquisition to get the customer to pay $12, where you’re only making four of it, is going to be anywhere from 50 to $100. So at the end of the day, she’s going to tell herself a whole bunch of lies for the next year or two until she goes broke and says, “Wow, I’m making 30 or 40% rate of return on on this customer.”
I’m buying something for X dollars and selling it for this, but then when she gets her financials done, she’s gonna realize that she’s losing her shirt. But I see this all the time. I see someone buys a trinket or a sprocket or a gidget gadget, whatever it is, they’re buying it for $5 and selling it for 10. Even if they’re selling it for for 15 and they’re going, wow, I’m tripling my money. No, you’re not, because if it costs you $100 to get that customer, then you’re losing money. Very simple. So, it’s that hidden, invisible profit column that people seem to like to ignore. And it’s funny because even when you look at these big, massive, publicly traded companies, they’re sitting on NASDAQ and they’re always talking about how much revenue. I was talking to a bigger company a few weeks back. Same story.
They lost $26 million in 2024. They managed to only lose $12 million in 2025. Halfway through 2026, they’re already past the 12 million they lost. Anyway, they ventured into some new technology and this and that, but they paid something like $18 million to acquisition this one company, which they probably could have just hired a bunch of tech guys and for $5,000 had the same technology. But bottom line is, I see even big massive companies, and nobody will ever admit they made a mistake. So what they do is once a year they just unload, they fire all their top CEOs and this guy and that guy, and bring in some new guys. But really, at the end of the day, they’re bringing in people who don’t know the industry. They’re just bringing in people who have acronyms and alphabets after their after their last name, and they think that look, we’ve really upgraded. Well, you’re still going to lose money unless you change the philosophical plan of what it is you’re doing. It’s sometimes it’s the architecture, and it’s like maybe maybe you need to raise your price, but we’re going to lose all our business. Well, you’re better off not doing any business than losing every time you do business.
Scott Ritzheimer
Absolutely, absolutely. One of the things that I think you have a knack to do is is to see things that others don’t, but but that’s inherently tricky, right? If nobody sees it, there’s probably a reason nobody sees it. How do you how do you help others to kind of see through the mist, if you will, to see the opportunity that that the general population would miss?
Sheldon Wolf
Well, there’s two types of people. There’s two people who pretend not to see it because they know it’s probably going to be their job, especially if they’re the ones who made the mistake. So they don’t want to point out their own error. They want to keep looking at that revenue column, which is looking nice and robust. The second guy is I see this often. He’s a great tech guy. He’s an amazing software guy. He’s built this awesome software for this industry, except he’s never worked a day in the industry. But the software is great, so of course people throw hundreds of millions of dollars into this great concept. But no one’s there to drive this thing.
No one’s there to really get this thing profitable, and I see that a lot too. So it’s not so much like the first guy who doesn’t want to point out something that’s to be his own demise. This guy genuinely doesn’t know any better. In his mind, it’s great software. What’s wrong? Why is this thing not just? Why aren’t people just lined up buying our software? Why aren’t people? Why isn’t everybody just using this? And and that is partially correct. It is great software, but if you don’t have the right people driving it, I’d rather have crappy software with awesome awesome people driving it. It’s like you know the old McDonald’s theory. They are not the best hamburger. End of story. But they came up with a way to sell a lot of burgers can’t argue with that, but they’re certainly not the best hamburger. But the guy who makes the best hamburgers usually in his own backyard, flipping burgers for his family, right?
Scott Ritzheimer
As a hobby and not a job. Yeah, yeah, yeah. All right, awesome. Well, Dominic, before I let you go, I’ve got two questions for you. One’s a real softball, but the other, before we get there, is this question that asks all my guests, and it is: What is the biggest secret that you wish wasn’t a secret at all for any founder, pre-founder out there watching or listening today? What would you like them to know?
Sheldon Wolf
It’s not so much a secret; it’s insight. I wish everybody had insight the way I do. Where I got my insight is experience. After over three decades of this, you tend to just instantly see something. I’ve already made that mistake. I made that mistake in 1996. I already saw that, or I already dealt with that recession. I already dealt with this wall that everyone hit. So you’ve been there, done that, and you get that from experience. But if I could just package a thing with a magic button that says hit this button every time you run into a problem. That’s just insight. That’s experience and insight. And I wish I could package that and give that to everyone who needs it. Because nothing better than successful entrepreneurs doing well and avoiding the obstacles. That that only experience lets you just walk around them these days. You know.
Scott Ritzheimer
Yeah, yeah, absolutely. If someone was sitting and listening, and you know, just piqued their curiosity, they were interested in learning more. Where could they reach out to you to maybe even glean some of that insight? But where can folks take a what would a next step be with you? Where can they reach out and hear more about the work?
Sheldon Wolf
You are more than welcome to contact me. You can reach me on LinkedIn. Easy to find under Sheldon Wolf. You’re also welcome to email me directly at sheldon [email protected]. Intellitary is i n t e l l i t a r y.com. I actually I’m old fashioned. I actually return email, and I actually will get back to you if you message me. Like I said, I’m I’m here to help. That’s that’s the fun for me. To me, it’s just adding adding another game to my day. You know,
Scott Ritzheimer
Fantastic, fantastic. Well, Sheldon, fascinating conversation. I love the approach to thinking about starting the right business, not just making your hobby one that has to pay the bills. And really appreciate you coming on. Thank you so much for being here today. For those of you watching and listening, you know your time and attention mean the world to us. I hope you got as much out of this conversation as I know I did, and I cannot wait to see you next time. Take care.
Scott Ritzheimer
Hey everyone, Scott Ritzheimer here. Thank you so much for listening to the Start Scale and Succeed podcast. I hope this episode gave you exactly what you need for the level you’re in right now. If you want to discover what level you’re in, take our 10 question Founders Evolution quiz for free at foundersquiz.com. That’s FoundersQuiz.com. It’ll pinpoint exactly where you are and give you tailored tips to move forward and reach that next level in your journey as a founder. If you got something out of today’s episode, don’t forget to subscribe, rate, or review. It helps us reach more founders like you, and let’s be honest, it means a ton to me, my team, and all our incredible guests. So keep starting, scaling, and succeeding, and I’ll see you in the next episode.
Contact Sheldon Wolf
Sheldon “The Wolf” Wolf is a serial entrepreneur, investor, and business architect with more than 30 years of experience in real estate, finance, lending, and technology. He spent his career identifying broken business models and redesigning them from the ground up. Today, he’s the founder and CEO of Intellitary, an AI-powered “Un-Brokerage” strategically engineered backward to scale rapidly, generate substantial recurring revenue, and maximize enterprise value. Sheldon believes the biggest opportunities aren’t found by improving existing industries—they’re created by seeing what everyone else misses and challenging assumptions others accept as fact.
Want to learn more about Sheldon Wolf’s work at Intellitary Real Estate & Mortgage Referral Network? Check out his website at https://intellitary.com/
Connect with Sheldon Wolf through his LinkedIn at https://www.linkedin.com/in/sheldon-wolf67/
Email Sheldon Wolf at [email protected]