Welcome to the Purpose Driven Investor, where we build more than portfolios, we build communities. I'm your host, Robert Howell, a real estate investor and founder of Define Communities. Each week, we'll explore how purpose and profit connect through affordable housing, land home packages, and impact-driven investing. If you're a lender, land seller, or a partner who believes money should move with meaning, you're in the right place. Hey everyone, welcome back to the Purpose Driven Investor Podcast. I'm your host, Robert, and today's episode is going to hit home for anyone trying to scale their real estate business without burning themselves out chasing leads. Our guest today is Luke Winter. He's a real estate investor turned marketing powerhouse and founder of Hello Pro. Luke didn't just study real estate from the sidelines. He built it. He scaled a flipping and wholesaling business to over 200 deals a year, lived in the chaos of lead flow acquisitions, you name it, uh, operations, and then successfully exited that business. And instead of walking away, he took everything that he learned, uh, everything that he faced. and founded Hello Pro, a nationwide advertising agency helping investors fill their pipelines using television advertising. What makes Luke's perspective so valuable is that he's learned from both sides of the table. And I think we'll enjoy that today and we'll hear all the different insights that he's able to share. So Thanks for having me, Robert. All right. Good deal. So Luke, let's start with your, uh, kind of how you, how you got started really as an operator first and a marketer second. Um, Yeah. So my initial. Forte into real estate investing was by accident. I became an accidental landlord. Like how a lot of people get into real estate investing is they just kind of stumble their way through it. So I was working in oil and gas at the time and moved from Illinois to Minnesota. And that was about 2011, 2012. I was pretty far upside down on a property that I was living in up and owned. And so in order to move, I needed to at least break even on the rental, uh, to clear my mortgage. And I didn't want to have to take money to closing, but I hired a property manager. We put a tenant in there that allowed me to move, meet my career goals and, uh, move to where I wanted to be at. And I looked at it and was like, man, I can break even on this. And I didn't even intentionally buy this to be a rental property. It was a personal property. I had no intention of ever needing to rent it out. Right. And I thought about that. And I was like, man, I could probably do this if I was a little bit more intentional and actually make money doing it. And so at the time, I had a pretty good career working in oil and gas and started to do some real estate investing on the side. So probably to I don't, my own, uh, lack of knowledge. I went, my next purchase was a six unit apartment building. Yeah. Yeah. Um, ended up getting like partial owner financing on it. So looking back, like I. Used a lot of the strategies that, um, a lot of the professional operators use at scale now, and I was just fumbling my way through it. Upgrading the units, got good bank financing that allowed me to renovate the property and do draws on that. So I didn't have a lot of cash into it. And over the course of time, I still own that apartment building, but over the course of the next 12 to 18 months, I over doubled the rents, which doubles the value of the property. And I started to enjoy real estate investing, but it was a lot of work. I'm managing the tenants, I self managed everything. And so I learned a lot of hard lessons about managing contractors and tenants and all the legalities of that process. Um, so I started to get into a little bit more like the fix and flip transactional type stuff, some wholesaling on the side. Uh, but again, it was very labor intensive and I didn't, I wasn't particularly looking for a second job at the time I was gainfully employed. I like more like the investment vehicle itself. So I kind of put that on the back burner for a little while. and got corporate burnout. and ended up quitting my oil and gas career after like 12 years in the industry and went in search of something more entrepreneurial and ended up crossing paths with a wholesaling and flipping organization that was doing maybe 30 or 40 deals a year. And I was an investor on their distribution list for deals. And they said, Hey, we need help with X, Y, and Z in our business. We need help with operations. We need help with KPIs and tracking. And that's exactly all the things that I was doing in heavy industrial space. So I was like, I can't not reach out. Like, you know, I'm not really looking for employment. I want some equity, I want partnership. And we ended up working out a deal. And we'll fast forward a little bit in the story. But about three and a half years later, we were doing about 200 deals a year, about 100 flips and about 100 wholesale deals. So it really scaled that business up substantially. So that's huge. Yeah, it went from accidental landlord Trying to navigate real estate, investing on my own to a couple hundred deals a year. I don't know, time span wise, Yeah, I love that. And I've got a similar story where I had owned real estate as a result of moving and having to rent it out because it didn't sell for one reason or another. When I got started, I did the same thing. I said, I've owned rental property. I want to intentionally own rental property. I don't consider myself an investor at that point because accidental investing, I mean, yeah, you're an investor, but not really. That's the way I got started too and said, I'm going to intentionally do it. I didn't start with a 16-unit apartment complex, but I started with $16,000 house in Memphis, Tennessee, and, uh, and then went to work. And it's crazy how just that one bit of action, then, you know, basically, uh, Yeah, exactly. And that was a bit, yeah, it was a great education. It was essentially like I got paid to get an education, you know, it was a playground. Uh, where I learned the ins and outs of managing tenants, managing contractors, and it's, um, a safe, safe ish place to, to fail, right? The mistakes on a 500 square foot studio apartment. Aren't that big when I hired the wrong contractor, you know what I mean? Versus, uh, trying to flip a dozen houses in a year. Mistakes can add up quickly there. So I got a pretty good understanding of, That's awesome. Love it. Talk to us about 200 deals a year. That's huge. Uh, what is, what, what, what's your business like, or what's it look like when you're doing 200 deals a Yeah, from a structure standpoint, um, you know, when you look at like a traditional fix and flip cash, home buying business, there's a lot of important seats in a business like that acquisitions is an important seat, uh, dispositions or getting rid of the properties that you own or want to wholesale as an important seat. Lead management's a very critical seat. A business like that has multiple people in each one of those spots. Then my role was really managing partner and COO, making sure that everything was efficient across each department, the handoffs were clean, that we were tracking our marketing performance. There's not a lot of people that sell their house for cash twice in the world. That's usually like a once-in-a-lifetime type event. You're really falling on hard times if you have to do it multiple times in your life. So you're generally starting each month from scratch, from the business operators perspective. So your sales and marketing is really the lifeblood of your business, and you really need to understand that that's a critically important part of your business. And so once you kind of wrap your head around that, most people really dial in their sales approach, their lead management, their follow ups. Most people really start to get into the nuts and bolts of detailed marketing and what's working, what's not working. How long does it take for a lead that comes in from TV, for example, to convert compared to a lead from direct mail or a paper lead provider? And so you start to identify those nuances in the business and start to accelerate what's working and do less of what's not working. And so, yeah, I think we ended up having maybe like a team of 20 ish people. You know, we were doing a fair number of rehab. So some people choose to outsource all of that. We had some internal resources, some external resources to manage that. And you just kind of take it day by day, step by step. It's a fast paced industry, Love it. That's great. That's a great overview. What's, what's one lesson that you learned from that period of time, managing that company, doing 200 deals a year that you'd want every investor to So in that time period, my biggest lesson was reflecting on my own growth and understanding how I operate is not how everybody else operates. And how everybody else's brains think is not the same way that my brain thinks. And so, as a leader of an organization that's sales heavy, marketing heavy, my mind is much more black and white, A or B. not gray area. So there's pros and cons to that. It makes me a good operator. I can understand technical concepts, but from connecting with team members or casting a vision, that in the early days was challenging. And so I had to evolve and adapt my leadership styles. to the team, because you're going to have a diverse team, right? You need to have people who are good at different things in your team, so understand how they like to communicate, and you have to meet them on their turf. You can't force them to come and adapt to your style. As a leader, you have to understand your team well enough to go and say, hey, this is how you like to receive information. This is how we get buy-in from the team. it might mean, hey, we have to plant an early seed before we roll out a big change with some people to make sure that they're bought into the concepts before we roll it out to the team, something like that. And so I would say, have a really good understanding of the team that you have and that you need to build, and go meet them on their turf from a communication and leadership style, and understand where your strengths and I love that. That's great. Great advice. So many times you just want to lead it the way you want to lead it, right? And you expect results and you don't get those results, but come to find out it started with you, right? And the way that you're leading. Exactly. Yeah. It's usually just boiled down to one person, why the team isn't moving in the right And that's usually the person in the mirror. That's funny. All right. Let's talk about the reality of scaling real estate. What was the hardest part about sustaining that scale that you were operating Um, I think from a marketing performance perspective, you have to have your pulse on marketing and understand the nuances of marketing. Very well. And that to no surprise is why I now have a marketing agency that helps real estate investors. But honestly, it's something that everybody needs to really dig into. And it's the lifeblood of your entire business. It's the oxygen for your business. Without quality marketing, you have no leads. Like I said, we're starting every month from scratch. So that That part is important and you know you want good quality partners with that or you want the technical aptitude inside your business in order to do it if nothing else you just need to know. how to be, you need to know enough to be dangerous in that space. You need to know how to set up a PPC. It doesn't mean you need to do it yourself, but you need to know, um, how to sort through what a good vendor does and what a bad vendor does. And you also need to understand how to measure the performance of your marketing with KPIs and stay ahead of the curve. Uh, you can't be waiting six months, 12 months to assess the performance. Um, The opportunity to evolve and change has to happen almost in real time. That, that that's very important. Um, so yeah, I would say KPIs understanding very deep, uh, you know, marketing aspects, just like you would get nuanced in your sales calls, how you handle the lead, how you handle, um, the site visit, how you handle the client experience. Uh, same level of Got it. All right. Love that. That's important. Important, real important in scale for sure. All right. Let's talk about your pivot from investor to marketing founder. Um, we'd love to know, you know, why, why marketing became your obsession? Why did you choose TV over digital and kind of what, what kind of gaps are you seeing? But, um, let's first talk about why you chose TV when Yeah, so maybe let's define digital. I would say from a traditional cash home buyer business, digital to me means PPC, social media, YouTube, you know, to define terms like there are TV channels that are digital and that's a lot of streaming conversations and most of our core strategies are centered around really old school TV, like broadcast media, the ABCs of the world, right? And so to no surprise, TV had a big impact on the growth of my business in Minnesota when we were scaling up and learned a lot of ins and outs of how agencies work, how different TV agencies can operate, what the difference is between a generic agency or one like mine that specializes in maybe just one industry and one product. So we're highly specialized in TV. We also do some radio ads when it's right for our clients. But that's really all we focus on. And we just try to be the best in that every day. And so there's a lot of value, in my opinion, that the clients get out of somebody that just focuses on one thing. And those are just lessons that you just learn over time and what a good service provider brings to the table and one that maybe doesn't have a specialization for real estate investors. You're probably getting upsold on things that you might not need. And so we help sift through all of that and just deliver what's going to get you results and what's going to get you the value that you're looking for. There's no upsells and things that aren't going to deliver results. So from my perspective, I like being a part of the real estate communities. I liked going to the mastermind groups. That's an important part of like my perspective on the world is you want to network and rub elbows with high achievers. And so I knew I wanted to help serve that type of client, people who are growth oriented, we just see eye to eye together. And, you know, I like being a part of those communities. And so from my perspective, like, well, how can I help those types of businesses, And through some of the knowledge and experience that I gained even after exiting my business, it started to shape this idea and seeing, hey, what else is possible for TV advertising and marketing? that's when I was like, okay, this is really starting to take shape. And I need to bring this to the, to the marketplace. You know, we're bringing tools, uh, to the marketplace that real estate investors didn't have access to before things that are reserved for the big boys of the TV marketing space that are spending a million a month. Um, you know, the Chevys of the world, the Fords of the world, they're spending a lot of money on marketing. They're not guessing. They're not guessing on what's working. They're not guessing on the creative that's working. They have tools to do that, and we've basically distilled down those tools and simplified those tools, so it is approachable for the real estate investor that might spend $5,000 to $10,000 a month on TV marketing, so that they can get better performance and have the same insights as the big dogs. And so for me, that's an important aspect of what we do and how we do it. And it is different from how it's served to real estate investors and options that were previously available. So for me, it was a good alignment of my skillset and the knowledge and also where I like to kind of operate and do Yep. Okay. That's awesome. I, yeah, I think there's lots of opportunity there to, to break through the noise. Right. So what, um, what types of, uh, investors should consider TV ads? And there's lots of, lots of different types of real estate investors. Is there a, a type of investor that TV ads work better than maybe Yeah, so generally the cash home buying businesses are going to be the best. They have a very strong value proposition. So if you like to buy distressed real estate, distressed single family homes, This is a great marketing channel. Commercial real estate, it gets more difficult. It's a really small pool of, of sellers, uh, much less than distressed residential. And generally they're not as motivated. So somebody distressed residential side, um, they're going to have high motivation factors. You know, they're. They inherited a property, they can't handle the payments on it. Um, they were going through challenging life circumstances. They need to sell. So it's a very compelling offer, um, that we can include in the ads. Uh, and even more so than like what a traditional real estate broker might be able to offer. Right. Uh, there's only so many businesses that will buy a house for cash and make a fair offer on it. And so if we can get that message out to the masses, uh, effectively. then you can get really great results out of it. And so we know we work pretty hard on the ad creative side and then the media buying side to get our clients those results. But generally, when people are first starting out on TV, They've got a pretty good digital footprint, so if you Google your business name, what shows up? Does your social media show up? Is your Google My Business page there with good reviews? People will look to make sure that you're legitimate, that you've got a track record, you don't have bad reviews, that type of stuff. And then TV marketing is generally a more expensive marketing channel. We want to have some momentum in the business and a proven sales process that gets results. We can't fix a bad sales process by just giving the team better leads. That generally doesn't work out very well. So fine tune that. And once you have a process that's giving you good results, then we can add gasoline to the fire. And so the other interesting thing about TV is it really helps boost all of the other marketing efforts that you're doing. So even if you're doing direct mail, for example, somebody will see the TV ad and then call the direct mail number because they didn't have time to write down the number from TV. So it helps all the other marketing work better, and it really emphasizes that omnichannel presence in your marketplace. So that's the other component too. We look for local operators who know what they're doing and who have some deal flow. The nationwide operators, you know, nationwide wholesaling is a popular strategy. These techniques don't really work well for those types of operations. We Got it. So when you talk about results, what's the typical timeline that your clients are Yeah, some get results quite quickly. I can never promise that. If you're first to market, if there's very limited competition, there's pent up demand, then you can get results quite quickly. If you're in a competitive marketplace, Um, you know, generally we see like a 30 to 60 day ramp up period, uh, where people will start, you know, you kind of start to become like a household name, you become memorable, recognizable, people know your tune, the jingle, that type of stuff. And so, you know, it. It can happen quickly, but realistically, in most markets, there's a couple-month ramp-up period before you start putting quality deals into your pipeline. But once you have that flywheel up and running and spinning, generally, Got it. And when you talk about results, what are the metrics that you use to say, hey, this is a successful campaign? Yeah, from my side, ROI, that's what was always important to me as an operator myself. So that's our ultimate metric. Are we getting good returns? A lot of people in the industry focus on leads and cost per leads. To me, leads are busy work. You want revenue. And so if we're able to drive revenue with less busy work, I think that's a good thing. And sometimes that makes people nervous. They're like, I only had 10 leads this month. Well, great. What was your ROI? Like, well, yeah, I did close one deal, you know, and it was a 70k deal on six grand and add spend like we're gonna keep doing that again and so yeah that's a conversation that i have with with boxes is low volume leads, very high quality leads high intent leads you don't get a lot of people saying like take me off your list you know i see your ad too much that doesn't exist. It's just people that want to do business with you. And so if you have a good lead management and sales process, and can handle those leads, well, you'll see those returns. And so, yeah, from an ROI perspective, like I usually like to try to get to three to four x, you know, over, let's say, a six to 12 month time span. And there's some places where we're doing much better than that, more than double that from an ROI perspective. But, you know, in a competitive marketplace, most businesses run quite well That's great. I'd take three to four X all day long. Yeah. Yeah. Especially without the operational headache of a lot of lead flow. Uh, you know, you look at some lower quality lead channels and it's a lot of operational overhead just to get somebody on the phone, just to connect with them for Yeah. Imagine when these sellers call they're, they're ready to sell today. Yeah. I like that. All right. So, um, we talked a little bit about leadership earlier. Um, and you know, I think with leadership, uh, part, part of being a leader is having the right mindset. Can you talk about what's the biggest minds mind mindset shift that Man, I reflect on my why a lot and I do need to hold myself accountable to it because you can drift. What's your why? Yeah, so my why is I'm pretty family focused and why I really went into entrepreneurship is to show my family what's possible in life. And I want to be a leader for my household, by example, for my two daughters. And so for my daughters to see what dad is able to achieve or what he's learned and what life lessons he's learned, I want to be able to go to my grave with those war stories, trials and tribulations, the ups and the downs that come along with being an entrepreneur. It's not all rainbows and sunshine every day. And so for me, I was I wasn't able to show them that in a corporate career. And not that there's anything wrong with that, but it was compelling of a vision enough and compelling enough of a why that I needed to make a change. And I needed to show them how, you know, how to be that leader and how to take that risk. And do you stray from that sometimes? Well, sure. And if I keep going back to that, it's starting to become more and more front and center in a lot of the conversations that I have with my kids, how we educate them, how we teach them lessons. And so for me, yeah, it's really focusing and tailoring the business to help support that and get the most out of it. Not from a financial perspective, but from a meeting my why and showing my family Five and almost three. Okay. Little Man, that's huge. I mean, by the time they're 10, they're going to be pro That's huge. I love that. Um, all right. And, uh, you talk a bit about family. How do you, how do you balance that ambition that you have as a leader, as an entrepreneur with your family, also with your sanity? That's a good question. And that's why I say I have to hold myself accountable to that sometimes because you can drift, right? Business is exciting and I really like helping entrepreneurs and I honestly sign myself up for more than I should in assisting the clients that are loyal to me. and helping them grow their business. But that's also what I would have wanted out of a vendor too. So from my perspective, though, you do need to find a balance of things that are fair for the business, fair for the clients, but also fair to my family too, so that I have the time and capacity to be present with them, to have a business that supports the lifestyle that they want. But it doesn't mean a whole lot if I'm tied up 24-7 on meetings, not present, that type of stuff. So we've structured a lot of our lifestyle to support that. Being an entrepreneur affords some flexibility. I can spend a couple hours with my girls every night, but then if I have to plug in and work a couple hours after they go to bed, that's fine by me. And to me, that checks a lot of boxes that are important. And so, you know, having that balance, I think is more about like an integration than finding a distinct dividing Yeah. I love, I love that word integration. Right. I think there's, there's so much to be said about that. It's, you know, I think the old school was. The balance was in order to have balance, you had to be done at five, right. Or you had to be done at four. Like there was a strict cutoff and now it's more about how do you blend and how do you integrate. Um, and this, the world that we're living in, right. It's, it's more of a virtual world. There's work happening everywhere. Um, sounds like you've integrated your kids and some of the work conversations that Yep. Yep. You got it. Yeah. Yeah. And again, maybe, maybe my why is different and that's how I run my, my family and have set up my business, but. Um, yeah, you know, everyone's on their own journey and in a different phase of business and life. So understanding those phases too is important, right? Uh, if you're in Yep. Yep. A hundred percent. All right, cool. So, uh, last, uh, bit of conversation here is a lightning round of questions. So I have five questions here that we'll just do a lightning round, uh, on. So what's the best deal that you've ever had or ever did? Um, we've had some, some banger deals, honestly, though. Uh, when I look back, like home flipping that wholesaling deals, like those are super exciting. There's been some fantastic deals there, but personally the apartment building, the first, basically my first intentional real estate investment opportunity and vehicle has delivered the That's huge. I think probably, probably from the apartment complex itself, but also what Oh yeah. Yeah. That's a good point. I didn't even think about it that way, but Yeah. That's cool. All right. Toughest lesson that you learned through this, either in the real estate investing or, or Uh, I would say, yeah, I would say from real estate investing, uh, Yep. So don't be greedy. If you got, you know, nobody ever went broke taking a profit. If there's opportunities on the table, go ahead and take it. But there were some hard lessons that I learned and that we learned as a business. You Yeah, I think that's important. All right. One marketing tip every investor needs. Do TV. It can really accelerate your business. I wouldn't be a good marketer if I didn't give myself a small plug on that. I wouldn't be in the business if I Yep. That's great. All right. A habit that transformed your productivity. You sound like a busy guy. One Um, honestly, I would say take, take the time to focus on your health. I've been, um, down a, a road the last couple of years, uh, with functional medicine, understanding more about how my body performs and also focus, um, on fitness and that has kind of unlocked another gear in my level of thinking and the energy that I have throughout the day. So, you know, from a productivity side, like invest an hour every few days, even in focusing on your fitness and man, like the clarity that I get out of that, the better sleep that I get and the more energy I have throughout the day is more Man, that's awesome. That's a good point. All right. Uh, that's challenging for me. Uh, I'm, I'm going to jump on that for sure. Um, all right. I think I know the answer to this last, last lightning round I mean, fulfill your mission, fulfill your vision for your life and your commitments to whoever is important to you, whether it's your family, your friends, people that have supported you along the way. But keep keep that vision front and center and keep keep that focused that that is. That is easy to lose sight of in the social media world that we live in. It's easy to look over the neighbor's fence and say, Hey, their life's better. But if you keep focused on what drives you and what, what you initially set off to do and to achieve, uh, I think fulfillment will Love it. Love it. All right. Great. Well, uh, Luke, I really appreciate you joining. Um, before we close out, Yeah, just go to my website, which is thehelloepro.com, or hit me up on social media, pretty straightforward name, Luke Winter, and All right. Good deal. Well, Luke, I appreciate it. And, uh, really thank you for the time and, uh, I know you're a busy guy. So for you to set aside 30 minutes to talk with us, uh, that's huge. And if you're an investor looking for a predictable way to attract motivated sellers, and you want to learn how this strategic marketing of TV advertising can actually move the needle, go check out Luke and the hello pro team. Thanks again, Luke. And we'll see you guys on the next episode. Thanks for listening to The Purpose Driven Investor. If today's episode sparked an idea or inspired you to make an impact, connect with me at howellandsons.com. Join our community of purpose-driven investors who are helping families find stable homes while building real returns. Because when