When you start playing with other people's money, you have to be right Yeah. As often as you possibly can, you know, and know how to mitigate risk. And that's maybe a whole other conversation, but, we've really had to sharpen our pencils or sharpen our tools to dial it in because we can't... Back to Unraveling IT: Expert Tech Talks, where we usually dive into the deep end of cybersecurity, cloud strategy, and why printers are still the greatest unsolved mystery of our time. I'm Garrett Wiesenberg, and today, we're switching gears. We're taking off the IT hat and putting on the business hat, which, let's be honest, still has a few tech stickers on it. My guest today is Drew Wiard. He started out in pharmacy and health care before trading prescriptions for properties. Fast forward a few years, and Drew's not just flipping houses. He's flipping entire business models. He's built an impressive portfolio of real estate, commercial ventures, and acquisitions that would make even Monopoly Man do a double take. What makes Drew fascinating for us in the tech world is how he's used technology to scale smarter, not as an IT guy, but as a business owner. From evaluating deals to managing operations from afar to experimenting with AI, he's proof that technology isn't just about uptime, it's about the upside. So today, we're digging in to how Drew evaluates deals, leverages data, and uses tech to build real world empires. One smart acquisition at a time. So, Drew, welcome. Can you just give us a little bit of your backstory and maybe tell us a little bit about how you went from pharmacy to, you know, maybe owning some residential properties to ultimately ending up where you're at today, is more commercial real estate and business acquisitions. Yeah. For sure. So, like you said, pharmacist by trade. I did that, graduated from Purdue in '05 and, did that for probably 15 and 17 years, something like that. But about halfway through that, just started buying one rental at a time right here in our hometown of Fort Wayne. Yeah. And it really wasn't to try to get rich or to quit my job or anything like that. It was more like, you know, I'm the sole breadwinner. Right? Yeah. So mom's at home, so just some security blanket money and things like that. But it just grew and grew and grew to the point where I could leave pharmacy. So I did, and really kind of doubled down on the real estate side of things. Yeah. Have acquired a couple of businesses, have enjoyed some elements and aspects of that. In the year that we've really, really refocused on commercial real estate and kinda scaling up to that next level. And, that's gone very, very well. It's been really gratifying. Like warehousing type facility? Industrial real estate. Most of those tend to be warehouses, but sometimes factories and manufacturing and stuff inside. And you had made it pretty high in the pharmacy world, all things considered. Right? You were like a director of pharmacy, if I recall or something? Yeah. That's right. I went into leadership right away. I did a residency, which most pharmacists don't. I got my MBA at night, which most pharmacists don't. But I knew that leadership was where I wanted to be, so I kinda jumped to it pretty quick. You kind of enjoyed being your own boss and setting your own schedule? Yeah. Yeah. Being bossy, I guess. Yeah. I guess. Yeah. You know, think for me, it was really more about trying to set myself apart. And, you know, when the robots come for our jobs, eventually, like, I wanted to have a skill set that was different than all the other pharmacists. Yeah. So that's the driver. Wow. So you mentioned commercial real estate and even acquiring some businesses. You know, with the businesses specifically, is there a reason you decided to, you know, acquire rather than start from scratch? Is that just kind of your overall portfolio idea? Or Yeah. No. It is very intentional. Startups are hard. And a lot of times, they don't work. That doesn't mean acquiring a mature business is any easier. But what it does mean is you're coming into a book of business that's generally established, at least on some level. Yeah. And given just the demographics of country and baby boomers and so many people having a business that they need to exit, but not having a plan for, I think there's a staggering amount of opportunity for those of us who are interested in such a thing. And so having been in leadership for a long time, but really wanting to have the ability to make my own decisions and set my own vision and goals for a team and all that was Yeah. Kind of the driver. Okay. Let's maybe go back a few years, you know, five, ten years ago when you were doing more residential real estate type transactions for long term rentals, things like that. Sure. What did the process typically look like for you when you were evaluating, you know, which properties to buy? Were you just, you know, perusing the MLS and hoping you came across something? Or Yeah. Back in the day, I mean, we would buy off of the MLS. There were actually deals that could be found there. Yeah. As time went on, that that certainly went away, and now it's almost impossible to buy a house, period. This is true. So it's definitely been an evolution as market cycles can continue to change, and inflation has changed, and all of that. But it did very much start with on-market properties, and then Really, really leaned into off-market property. And when it came to, you know, running your numbers and trying to evaluate, is this a good deal for me? Was that just Excel? Was that, you know, paper pencil? What did that kind of look like? I tend to be pretty analytical. I like my spreadsheets and all of that. Yep. So it was definitely by the time we formally put that offer in, yes, it's gone through the spreadsheet. It's, you know, hyper analyzed. You get good at it though, and it's enough of a volume game that you quickly like, you can kinda glance at it and see numbers from a high level. And if it looks good, then you push forward. And Yep. So, cursory review, napkin math, but it's going through the spreadsheet before you transact. And how has that changed today with, obviously, the introduction of AI and other SaaS based applications and things that are available to you? Yeah. Honestly, it's kind of changed wildly. You learn of through the school of hard knocks that when you're playing real estate, you don't wanna play feel estate. Right? Like, people getting their feelings. Right? They love that building. That's a that's a great Yeah. Yeah. So it's When you play at a higher level with the commercial real estate stuff, like, there is no margin for error Because these are million dollar buildings, not hundred thousand dollar Yeah. Buildings. Right? And so the underwriting just needs to be more sophisticated. The tenants are more sophisticated or complex, maybe Yeah. Is a is a better way to put So as time goes on, you have more advanced spreadsheets, you have different tools, you learn different ways to underwrite deals. My partner, who is a walking abacus, and he's brilliant. He was super, super brilliant. He and I kinda said, and we've, you know, dialed in the right tools, but he really has an affinity for taking Excel and kind of melding it with AI to build some really, really powerful tools. And if you were to look at it, you would just see a spreadsheet. What we see is the hours that we built, allowing us to put a couple of inputs in and get an output that helps us make decisions on a much faster volume based level than we ever could have before. Interesting. And it's interesting that you say feel estate, because I imagine that with residential real estate, that's far more common even than in in business real estate or commercial real estate. I'm sure you still have some of that. But Yeah. You know, I just sold my home recently, and I was very attached to it. I'm sure that was a pain to work with. Emotional. Yeah. Isn't it? Yeah. Because it's your baby, you know? Yeah. I think when it's your home, it's a whole different thing. Right? It's okay to play field estate on that front. But when you go to invest, like, you need to know your criteria And it's just very easy to get romantic about buildings and houses and all that. And I've been guilty as well. You know, you look at a project and it's gonna be a great flip and you can do the tile shower here. You can do, you know, the porch out back. But if it doesn't underwrite to a proper Yeah. ROI, then it's all for naught. But we see it in commercial as well. Like, I will see a building that I'm like, oh, that's the one. Like, we're gonna go get that. And you put it through the tools and it like, the numbers just don't- Don't make sense. Yeah. And so you've gotten to a point where it's truly just a numbers game for you. I mean, it probably has to be to an extent. It is. And, you know, you have some flexibility, you know, some ranges and things that you can work within, but we also take on a lot of investor capital. So we have money in our deals, but we invest for other people as well. And that's kind of the second head of our business is, yes, we buy investment commercial real estate, but we provide investment opportunities for people who wanna be outside of the stock market and things like that. And when you start playing with other people's money, you have to be right Yeah. As often as you possibly can, you know, and know how to mitigate risk. And that's maybe a whole other conversation. But, we've really had to sharpen our pencils or sharpen our tools to dial it in because we can't be- Yeah. That makes sense. So going back to what you had said about, you know, building out some Excel spreadsheets with kind of AI built in, you put in a few inputs and it outputs Yep. You know, what you need and saves you a lot of time. Are you finding that that's more accurate as well? Is there an accuracy gain here as well, or is it strictly just a time-based gain? I don't know that I can say it's more accurate. I feel pretty good about underwriting before. Because most of what's there is our thoughts and our process, but we were able to take thirty steps out of it. Now it's five steps. You know? It just deals are hard to get whether you're residential, industrial, commercial. Like, it's just hard right now. And so you have to throw, you know, a hundred lines in the water and hope to get one fish. Right. And so we need to be able to underwrite at a high for a while, that was the rate limiting step. We've now eliminated that as the rate limiting step, and now we have other challenges, you know, other bottlenecks that we gotta Work through. So let's dive into some of the businesses you've acquired. You know, how involved are you in day to day? Or were you just the individual who came in, acquired it, and you've got somebody else running that 24/7? You just kind of- Yeah. Good question. So it's evolved over time. We bought manufacturing facilities, and we rolled up a few and merged with a few. The intent is really to be present and on-site about one out of every four weeks. The goal is, you know, for us, when we acquire, we wanna have a good operator, you know, a good COO or Yep. Whatever that title is. And that has worked very well for us. You know, we've merged with some other folks, and they've really been the specialists in that field. And they drive the bulk of the day to day. And I've enjoyed that experience. I for the most part, it's been very positive. It has highlighted that we really do love the real estate thing. And Yeah. It's kind of like what our we are uniquely good at that. I could probably buy and roll up some other businesses, but, I mean, I'm edging into being an old man, and I eventually, I'm gonna retire. Right? I'm not I don't have the energy that you have anymore. So I mean, I'm getting there too. Yeah. Baby steps. Yeah. Baby steps. But, you know, as I look at, like, what do the next ten years look like? I would like to be able to you know, I do a bunch of flying. I do a lot of riding. I wanna do that at the drop of a hat. And if you're not stuck, but if you choose to build a business that requires a ton of your time, then that's the life you get to live. And there aren't too many off ramps if you decide you wanna change it. Whereas investment real estate, if one of my parents gets sick, I can just go be with them for a month. Like, I can just do that. Yeah. You have the flexibility? Yes. We're leaning more and more into that. So, I mean, with those businesses though, and this is probably my final question on those businesses, but do you at all worry about your cybersecurity posture, your IT posture, anything like that? Does that keep you up at night at all? I don't know that it keeps us up at night, but that might be out of naivety. Yeah. One thing that I had never thought about at all was insurance coverage for cyber security type of It had never even crossed my radar. And we acquired the first business, someone suggested it, so we started digging into it. So we purchased it. We haven't had to use that policy, but we have since had, you know, a few, I guess, I don't know what you would call it. Breaches or incidents? Yeah. Exactly. Where, you know, there was a six figure money hole that we had to unwind and figure out. And so my appreciation for the importance of it has really escalated. Yeah. That makes sense. I figured you wouldn't have much exposure it considering you've primarily done real estate investment and pharmacy. I'm sure it was kind of just off to the side. It wasn't, you know, front of house. Yeah. Even at the hospital, I mean, the large corporations that were way outside. I mean, they had the whole IT department. Yeah. Some of that's probably in house or out. Yeah. You know? You just knew what you could do on your computer and what you were, you know Yeah. Log in, log out. Yeah. Log in, log out. Yep. I wish there was a fun name for that, like, feel estate. We'll work on one. Yeah. We'll we'll- Around when I We'll workshop one. Too. But, you know, speaking of, flying, you know, just for our viewership, do you wanna define that a little bit? Because I I don't think people will quite understand what Betty the Butt Fan is. No. No. It strikes people a little odd. So I fly a paramotor. And for those who don't know, like, if we lived in the mountains, we would just go paragliding. You don't need a fan. You don't need a motor. But here, we don't have mountains. Right? So if you wanna get airborne, you have to strap on a fan. And so, Betty the Butt Fan is is my Butt Fan. And there are actually three Betty's. People don't know that. Really? Yeah. In the garage, there's three Betty's. And they have the two person a two seater. Right? I did for a while. I I sold it because, you know, I gave a ride to everyone that I wanted to give a ride, but then it was everybody else who wanted one, and I had to take the time to do it. And they think I'm generous with my time. You're not as much as you probably should be. So That's the old man coming out. Right? It is cantankerous, man. I'm slowly turning into a curmudgeon, but so it has been sold. But I fly as much as I can, and I ride all the things and drive all the things. But that's been really your vision from the start. Right? And I think you've already touched on that a little bit, to be able to do what you need to do or have the freedom to choose what to do and when to do it. That's it. What I wanna do, when I wanna do it, with whoever I want, wherever I wanna do it. Yeah. And that sounds wild and extreme, but that could be taking care of your parents who have cancer. Yep. Like my daughter, she's gonna move to Tampa. She's gonna go trial it for a month. Right? Well, if I wanna go help her move in for two or three weeks Yeah. Help her get it settled, then we just do that. Yeah. You know? And if it's working eighty hour weeks, well, that's your choice. Right? And you're the one choosing, hey. I'm gonna go work eighty hour weeks. Well, and I can take it with me too. Yeah. Right? I mean, there are I tend to work really hard. It's not that I just wanna skate, but I you know, this week, I will hustle like mad. Next week, I'll dial it back because I wanna do something fun. You know, I wanna have that flexibility and just be able to adjust with the seasons of life. You know, we're it'll be a number of years before grandkids come, but I'm sure that'll bring, like, a whole different season of what I want flexibility and work life to look like. Yeah. Well, and you have, obviously, even though you don't necessarily run your standard business, so to speak, where you've got employees, they come in, sit down, like, you don't necessarily do that. But I'm sure you take IT and cybersecurity somewhat seriously with your personal- For sure. Information, like your work information. Because I'm sure that you've got quite a few financial numbers and confidential documents. What what are you doing, you know, today to secure those? Yeah. I you know, we do really have to think about it. We in times past with our investors, you start with friends and family. Right? So they trust you. Right? They give you a lot of financial information because they're investing with you. And only recently have we moved to an encrypted platform where they go in and they put their numbers in. We should have done that a long time ago. That's just one example of things that we just hadn't really thought about. Yeah. You know, most of our systems, at least on the cybersecurity front, are pretty basic. I mean, they can be things that we can manage ourselves or software systems that we can hire. As we grow and more people want to invest with us and we buy larger assets, we are going to have to start filing with the SEC and all those regulations and things that come with it and the software systems that come along with that. You know, we'll have to do some study and figure out, like, what's the next level of sophistication on the IT side that Yeah. Matches the sophistication of what we're doing on the real estate side. And I I don't know how to answer that yet because we're not there yet. Yeah. We're knocking on the door. I was gonna say, you're buying quite a few large apartment complexes in in Phoenix, Arizona and other locations as well. Right? Like, multi unit- I'm invested with the groups that that do own those. Okay. My group specifically buys industrial flex warehousing mostly in the Midwest, but we closed one in New Mexico Oh, wow. Okay. Couple days ago. Nice. Is that why you had to reschedule last week? That is literally why we had to reschedule last week because we market directly to people who own these buildings. Yep. And when they call and say, okay, come talk to me about it, like, I'm- You're- no. I don't blame you're dropping everything to go and sign on that dotted line. Yeah. Our, COO once told me that time kills all deals. It always does, especially in real estate. It's probably true every time. And that's something that's really stuck with me. Obviously, you know, we do sales here as well, and it's the longer you let it sit, if you don't pounce on the opportunity immediately, the likelihood that that sale is lost is Well, they're either gonna change their mind. Yeah. So you gotta strike while the iron's hot or someone's gonna come in and get the deal that someone was trying to give you. Yeah. Which is why used car salesman are so pushy. That's one reason. Yeah. Well, that's one reason. Yeah. So let's maybe look ahead to the future. Obviously, ten years ago, it was a lot of just Excel documents, lot of your time building out these things. Now, you've got a little more automation built in, some, you know, AI kind of incorporated to maybe help evaluate. Yep. What do you think five to ten years looks like? I think it'll be really interesting. So we do kind of have a five year vision set, but it's really like the next 24 to 72 months that we are laser focused on growth And acquisitions. And I think that's a rabbit hole we could go down, but it has to do with the real estate market and what we think is gonna happen on that front. So right now, it's growth Great. Growth. Yeah. Three to five years, we'll have to reassess to see where the market's at and that asset class and all of that. But my guess is we kind of settle into management as opposed to growth. Okay. And then strategically move in and out of assets as the opportunities present themselves. But we've slowly started bringing more team members on, you know, admin assistants, transaction coordinators. I onboarded a sales team member this morning. Come on. A lot of those things, I think, you know, AI will help us to automate. But when you're running a skeleton crew, you still probably need one person who's accountable Yeah. For getting that process done. Now, maybe I only need that person 10 hours a week instead of 30, and And so I see the potential for that. But I would think probably a team of five or six people is what we see. Yeah. And, yeah, I don't know I don't know that answers the question, but I don't I don't think it'll be wildly different. I mean, does, and I I'm kind of viewing it as well from the perspective of having recently just bought and sold a home, you know, myself personally. Yeah. I used a lot of ChatGPT to run, you know, market analysis or do different things for me based on what it could find on Zillow, Redfin Right. You know, realtor dot com, whatever. Yep. And I was just curious if, you know, you would expect to see some of that as well, but maybe on a more larger scale through the MLS. Like AI built into that to give investors what they need. Well, AI is gonna be built into everything because they have to sell it and you Absolutely. If you just put the star and the AI text to it or something. Right? And we use Gemini heavily because we live in the Googleverse, Google Phone, Google Watch, Google everything. I'm sorry. For I know for better or for worse, but I'm old and cantankerous, so I'm not changing at this point. But I do think that there are things that I just can't really even think of. So for example, one of the tools that we've implemented is we've started leaning on Instantly AI, which does a lot of different things, but we market directly to sellers. Right? And if we were cold emailing from Google, you're gonna get marked spam and it's flagged and all that instantly does a really nice job of kind of mixing that up and spreading the times and changing the message and all of it. It's phenomenal. Yeah. Right? And so that's an example of a software that didn't exist, I don't know, 12 to 24 months ago that, I mean, we're leaning on and it's changing the game for us. So I imagine that there are gonna be software solutions coming, AI solutions that we're just not even thinking. You even know, like, what problem it's gonna be solving, but there's gonna be some Yeah. It's a thing like, you know, like you said, it's gonna solve a problem. Today, don't even see it as a problem because that's the nature of the business. Like, they're just doing it. So I don't I mean, I don't think any of us five years ago would have expected that, you know, you could just put a prompt into a computer and have it spit out a 24 page document on why you should do or not do something or Yeah. Yeah. Well, and we use it a lot for legal review and not that it is the lawyer, but like No. We've got some legal stuff going on and you get some documents. We run it through and say, hey, what does Michigan think about this? What does Indiana think about this? And then you can take that back to the lawyer, and they say, yeah, that's good idea, or no, that's nonsense. But it I don't know. It just gives you it's just such a powerful thought partner, and that's really where I'm trying to lean into it as much as anything is to like, I talk to it, like, when I'm on my walks and stuff. Like, we just banter back and forth to help create It gives you a space to air out your thoughts and have somebody else evaluate them or provide feedback on them, I think. Help me think of things that I hadn't thought of. Yeah. Like, what am I missing in this thought process? What could I be doing differently? How could I frame this differently? Yep. For sure. Yeah. I've used it for legal documents as well, it's great because it'll just summarize it. Because, I mean, you've read through legal documents. It can be it can be awful. Yeah. Yeah. And sometimes it says things that you don't know how what it's even saying. Yeah. Legalese is not No. Easy to interpret. No. Not at all. So you see it as more of a an enabler rather than a replacer, essentially, would be fair. I think it's probably reasonable. I haven't thought about it through that lens. So I you know, I'm a big fan of AI and where it's headed. You know? Now we could have a whole different conversation about tech and our kids and devices and how much time I spend on my device, not that Probably a conversation that should be had at some point by we would have had it ten or fifteen years ago. Yeah. I like, when people ask me, how do you raise good kids and all that, you know, fortunately, their mother had a lot to do with it. But I would go back and change all of that Parameters and expectations for the expectations for the house and standards for how we live and how we integrate tech. And as a tech guy who really loves it, I would have next to none of it Yeah. Till my kids are sixteen, seventeen, eighteen. Yeah. But that that's a whole different soapbox. I mean, I'm kinda right there as well. I mean, I've got a five year old at home and Yeah. I'm at the point where I don't want him to have a cell phone. I don't want him to ever have a computer in his room or a TV in his room and Right. It's shared devices. It's in central locations and it's only used very sparingly Right. For whatever you may need. But unfortunately, the world today, I mean, it's going more technical. Right? So, I mean, good or bad? Yeah. You know, schools are e learning. Yeah. And I mean, these are all good things. I mean, like, I'm not against the tech. I'm just against our shortened attention span Yeah. You know, the addiction to dopamine, the fact that no one goes out and does anything. Yeah. I see our teens and our young people struggling to interact, and it's a conversation that should be had. Oh, I completely agree. Well, kind of segueing directly from you hate IT, you know, what's the one piece of technology you can't live without today? The problem is I love IT. So Yeah. Knowing that I need to distance myself from it from time to time just for my own mental health is a struggle because I do love it. Hit me with the question again. What's the one piece of technology you couldn't live without? Good lord. I don't even know. Spotify. Probably. Spotify Premium for fifteen years. For music or for podcasts or both? Yes. Okay. Spot I didn't realize that Spotify Premium, you get like audio books. Yep. Like, that I was paying for on Audible, which is just nonsense. Yep. Tech I couldn't live without. Man, I even still, I don't know. It's either my CRM for lead generation, or it's gonna be just spreadsheets, because our work is just so analytical. I just don't know how we would do it without it. Now, how we use it in today is wildly different than we did even two years ago, and I'm sure it'll be wildly different in the future. But I don't know. That's probably my answer. Okay. That's a fair answer. Yeah. It's definitely not a wrong answer. Sure. Well, you know, I really appreciate you being here today, Drew. I do ask kind of one parting question of everybody that kind of comes through, and it's typically, you know, what piece of advice would you have for someone who may wanna get into real estate investing or someone who may not be familiar with that world as a whole? You know, what would you say to them today to maybe encourage them to look into it? Yeah. You know, just to jump in or how did they get involved? Yeah. It's for some people, it's a discouraging space because they think they can't do it now or it's harder now or, you know, Drew, you got in when it was easy. I hustled like a maniac back in the day, and you can absolutely get into it today. Yep. I would say I mean, it requires it's like with anything. You've gotta study, you've gotta learn. But I think you learn a lot from people. So find people who are doing it. And the one thing I would leave you with is do not take real estate investment advice from people who do not invest in real estate. Because everyone will tell you why you shouldn't, and they don't own Jack. Yep. So talk to people who have done it, who have made money, who've lost money, and who are in the trenches. That's who you're gonna learn from, and tune everybody else out. Yeah. That's great advice. Thank you again for coming in today. Appreciate you dressing up for the occasion as well. As always. And we'll, we'll catch you again sometime in another episode. For sure. Thank you so much. Yep. You bet. That was Drew Wiard, a perfect example of how business leaders are using technology not for the sake of it, but to create real leverage. What I really loved about Drew's story is that he's not buried in the tech. He's focused on the results. So whether it's evaluating acquisitions, modernizing operations, or even just experimenting with AI, he's using technology to scale without chaos. And that's really the takeaway for anyone in IT. Technology is not the finish line. It's the multiplier. The goal isn't more tools. It's more impact. It's about creating smarter businesses, faster decisions, and outcomes that actually matter. Because at the end of the day, technology is only as powerful as the strategy guiding it. I'm Garrett Wiesenberg, and this has been Unraveling IT: Expert Tech Talks. Thanks for listening.
