What is a more inspiring success story than a success that sprouted from humble beginnings? At such a young age, our guest’s mind was enlightened on the essence of financial independence—learning from her environment in the academe and observing her family’s financial dynamics.

In this week’s episode, Craig and Zeona get to meet such an empowered woman of her own name. Ashley Wilson is one “badass” in the commercial real estate field, owning over 700 units on this date of writing. Exploring from house-hacking, and house-flipping, to multifamily, such extensive experience has established her place in the industry. If you’re lost in trajectory or just need that push to kickstart your goals, this episode is a sign. As Ashley is the embodiment of never regretting taking action, you will never regret preparing to lend your ears and be devoured by the grit and intellect of such a real estate powerhouse!

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The Importance of Drive, Hard Work and Connections, Even at a Young Age With Ashley Wilson

We’re here to talk about Ashley Wilson, who has such an incredible story about really just starting off as a house hacker and now she’s transitioned all the way into commercial and so she kind of took her journey step by step and I think it’s just like such an amazing story. What do you think, Z?


Yeah, you know what I really liked about Ashley is that she’s incredibly smart. I mean, I knew she was a badass in real estate, I did not know any of this other stuff about her whole earlier career. I feel like she lived 10 lifetimes. But what I love is that she’s so smart and she’s still in real estate and it just makes me feel so freakin’ validated that I am in the right field.


Yeah, and you could tell how smart she is by the way she answered the final question, like our fourth kind of joke of a question, and how much she processed that and how much she analyzed that. I was like, damn, usually people are just like, boom, there’s your answer but she really like analyzed and gave a great answer so make sure you listen all the way to the end to that point. And so, yeah, let’s bring Ashley on the show.

Ashley Wilson, how are you doing today?


I’m doing great. How are you guys?


We are doing fantastic and we are super excited to have you on the show. I feel like — actually I’ve heard a lot about you. I don’t know, have we ever met? I don’t know if we’ve ever met in person.


I think we’ve probably met in passing but we’ve never had a conversation, let’s put it that way.


I am shocked to hear that.


I’ve never had that pleasure and it sounds like today is my lucky day because we get to sit down and have an hour conversation. So why don’t we just start it from the beginning as to where you first heard about financial independence?


Financial independence, that is a great question. I mean, I’ve seen it in action as a child. I saw it because I went to private school. I was very fortunate to go to private school when I was younger and not through my family but through other families that I went to school with, it was very obvious to see kind of the haves and the have-nots, especially the presence of families being around during not only important occasions like, for example, recitals or sporting events but also day to day, like parents volunteering at school. So, I saw it in action at a very young age and it had a huge influence on me. But then, in terms of the first time I realized that it was within my grasp of reach was definitely post college. I always had a drive to achieve it but I didn’t realize that I actually could achieve it until after college and educating myself on all different financial opportunities and investment opportunities that were out there.


Okay, I’m kind of curious, because it seems like there’s a lot of different bubbles, and I feel like we’re in a financial independence bubble and some people are in their like mom bubbles and so going to this private school, you maybe we’re in a little bit of a bubble but you noticed that your family maybe didn’t quite fit in. And so help people recognize that, like what was something that your family did that others didn’t do or vice versa that made you realize that, hey, my parents aren’t on this financial independence track but my friend Jesse is?


A couple of things. First, both of my parents worked, which was a huge differentiator. I also purchased all of my school uniforms through like the hand me down consignment shop that the school offered as opposed to the majority of my friends purchased all of their uniforms brand new. When we had dress down day or non-uniform days, a lot of my friends every single time had a new outfit or a new outfit for the dance and I didn’t always have that. So, there were things like that that were impactful and also my friends’ parents would be at every single parent volunteer and my parents, they came to a lot of events but they couldn’t take off in the middle of the week. They normally could come to the evening events and weekend events but I know how much my parents did to provide these opportunities for my brother and myself and everything from when I would go over to their houses and they had mansions and nannies and we were in like, I think it was 1,700-square-foot, one-bathroom, really one-bedroom but they converted a closet into a bedroom and they converted the attic into another bedroom. That was different than everyone else that I went to school with. So, it was a completely different environment from a lot of my friends versus what I grew up in.


I’m really curious, like the way what you know now about private school, like it seems like such a good opportunity but actually wasn’t? Like would you have recommended that again? Would you have done it again, just seeing how different your life was compared to everybody else?


I 100 percent would do it all over again because I think it instilled drive and hard work and the importance of connections. I, to this day, say that you can get a good education anywhere, what you’re paying for in private school is the connections. You’re not paying for the education. You can get a good education even at a public school or a state school, parochial school, but you’re really paying for the connections and the opportunities. I can tell you firsthand that the schools that I’ve gone to have been a huge influencer in the path that I’ve been able to take just because kind of like name dropping. My first job out of college I was able to get because someone saw on my resume and I put my high school on my resume because I knew it had that power but I went to the oldest all-boys — I think it’s the oldest all-boys boarding school in the entire country and when it went coed, it was the hardest school to get into in the country for women because they were taking such a small amount of women that first year so the chances of getting into the school were very rare and I was able to get in so that was something that signified a level of prestige that I was able to play off of. So, I definitely think private school had a huge impact on my success.


I just want to highlight for people that if you are past the age of school and you can’t really go do that again, there are other ways to make these connections. So, some of them are through masterminds or coaching or even just going to conferences, like I shared a cab with Ashley and that’s how we met the first time, but it’s just putting yourself out there and getting close to these people. Of course, it’s better through a long connection like school, but just knowing that you guys can still access this and it doesn’t have to cost a million dollars. Craig?


Yeah, piggyback off of that, and everyone is dealt their own hand, right? Some people, maybe the strong card in your hand was that you got to go to private school and you had connections but it didn’t sound like you had a whole lot of money anyway because compared to your friends at school, you were kind of like the poor kid. While that may not have benefited you immediately, but you saw that that’s not what you wanted and so that was your drive, I imagine, to then go ahead and provide that for your kids and while I went to public schools and so I didn’t have the private school thing, but I had the rough around the edges, work hard, all that kind of thing and I saw that’s what my parents did and I think that’s what got me to where I am today. Z, I know you’ve got your own story as well and so, wherever you are right now, look at what hand you’ve been dealt and play it the best way you can because there’s infinite ways to success, you just got to figure out how to get there. And so, Ashley, so you went through this great boarding school, it sounds like you then went ahead and went on to college. What did you study in college? Were you thinking that you wanted to go into real estate this whole time? Where are you at now?


It actually ties into the original question you guys asked because whenever I was asked what I wanted to be in life, it always centered around my knowledge of whatever was the highest paying job that I knew of at that time. So, there are a lot of kids who always wanted to be a doctor or a firefighter. I never was like that. I was always kind of changing until I got into college and then I kind of really honed in on what I wanted to do and I wanted to be a neuropsychologist and I wanted to study concussions in professional athletes. I figured that was something that interests me, I was an athlete, I love neuroscience, I love psychology, and I could blend the two together, make a lot of money doing it and have my own schedule. And that was my ultimate goal because even though I did grow up as perfectly as you said it, Craig, in terms of being the poor kid compared to my friends, my parents still prioritized and supported my brother and myself and that was something that I valued. And I always said that whatever I did, I wanted to be there for my family. That was the number one thing, and I didn’t have a family at the time but I knew that was going to be really important to me so what I did is after school, I took a year off and then I wanted to go back to med school and I took a temp position at Sanofi-Aventis in their CNS, central nervous system department, which does psychology and, neurological indications for, like I worked on the Ambien team, they do major depression disorder, they do schizophrenia, they worked on all these different drugs and I was temping there for a year and the director asked me to bring in the New England Journal of Medicine and I had read it in undergrad and I brought it in and I was like, “Oh, this is actually a really great issue, especially this one article,” and I started talking to him about it and he was like, “You read the New England Journal of Medicine? Why are you temping as an admin here?” and I was like, “Oh, well, I’m taking a year off and then I’m gonna be a neuropsychologist,” and I told him, he scheduled an appointment, he said, “Okay, find the next available spot I have on my calendar, we’re gonna have a meeting and I’m gonna convince you why that’s a bad idea.” And he convinced me and he said, “You know, you can get — your ultimate goal is to be there for your family, you’re not gonna be there for your family if this is what you’re doing,” so what I ended up doing was I ended up having a position created for me, so they literally created a position for me and I worked in pharma thinking that my path to having this financial freedom was going to be a CEO of a top five pharmaceutical company, so that was my new objective. And I was not far from it when I left pharma. So, I kept getting promoted, I got my master’s full time, while working full time, and I kept going up the ranks because I was so driven and I was so set on having this corner office CEO title that was going to lead to my financial freedom.

The irony of the whole situation is the further I got along my career path, the less time I was spending with this new family I was developing. Click To Tweet

I started dating my now husband and then we got engaged and got married and it was very quickly noted that, all of a sudden, I was spending more time, 130 hours a week about on average, working and no time with him so it was doing kind of the opposite of what I initially had set out to do.


I love that. That’s kind of such a unique story where you kind of started off in the medical field and then transitioned. How long were you in the medical? You graduate college at you say 22, 23, how long were you then in the medical field for before you then came to that realization?


So that was in 2014, I left, 2013, 2014, I can’t remember. I think it was 2013 I left and I started in 2005.


Okay, okay, so you did it about eight, nine years in the medical field, you said, “Okay, no way, I don’t — this is the exact opposite of what I want. Sure I’m making good money but I’m —” dollar per hour, maybe you’re not making great money because it is so much time. And then is that when you kind of hopped over to the real estate game?


Kind of but not really. So I actually hopped over before that but I also want to say the best quote that I think captures exactly what happened to me was in Brandon Turner’s Intention Journal in the intro which says, “People spend their entire life climbing up a ladder only to get to the top and realize it’s against the wrong wall,” and that was what had happened to me. So I always remember that because it kind of resonates with me on exactly what I was doing, but with respect to real estate, I actually started real estate in 2009. I started listening to BiggerPockets in 2007 so my husband introduced it to me, he was listening to it, he introduced it to me, he was looking for an alternative asset class to invest in besides the stock market, he wasn’t a firm believer in the stock market. He looked at multiple asset classes, landed on real estate, introduced me to BiggerPockets, I started listening to them, listening to the podcasts, on their forum, everything in 2007 through 2009. We bought our first investment in 2009.


I love that you brought up your husband because I just like want to talk about him, because I haven’t really interacted with him but I’ve heard a lot of stories about him and I know that he is really excited about being a trophy husband and he takes care of your family and he’s like the one who’s there all the time with the kids. So, how was it for him? Like was he watching you and just really supportive when you were working 130 plus hours a week? Or was he really, it sounds like he was feeding you this BiggerPockets thing going like, “Hey, we’re gonna go this other direction”? How was it for him this whole time?


He introduced it to me not as, “This is gonna be our full-time gig,” he introduced it to me as, “This is gonna be our side hustle.” So that was kind of what I always thought about real estate and the irony of it is we were really successful when we started investing in real estate but we kind of didn’t really pay attention to it because we didn’t have the mental bandwidth to pay attention to it. I was working the 130-hour weeks like I had automated it because I didn’t have the bandwidth to pay attention to it. So, yeah, the money is great coming in but I wasn’t in the right mindset to say, “Hey, I’m doing it on this scale. Imagine if we scaled it exponentially, how much more lucrative we could be at this asset,” and he was a professional ice hockey player so he was entrenched in his own career that he didn’t have the bandwidth either to pay attention to real estate. So we just kind of did it on the side, like I jokingly say we were lazy when we started with real estate.

It wasn’t that we were lazy, really, it was that we didn’t have the bandwidth to pay attention to it. Click To Tweet

So it wasn’t in — and he was supportive of me wanting to get to the top level and he knew I could. He knew I have a crazy drive and he knew I could do it. He was not happy about how much time I was spending on it versus him. So he was actually the precursor for me leaving pharma at the end of the day.


That makes sense. So, BiggerPockets, I wasn’t in that, like I wasn’t aware of it that early on. I think I probably came around 2014, maybe ’15, something like that, so I’m not sure what they were talking about that early in the game, but did you guys just start with a single family rental? What kind of was your entry point?


We started with a house hack. So we started with a house hack, turned into short-term rentals. Airbnb, I recently found out it was a company when we started but it wasn’t the preferred company. Vrbo led the market, that’s where everyone looked to look for short-term rentals. No one even called it Airbnb, like, “We did Airbnb,” like everyone said, “Oh, we have a short-term rental through Vrbo,” that’s how people would talk about it. So we started with that. Then we did long-term rentals, then we did, my dad and I started a flipping business, a high-end flipping business that we’ve had for eight years and then we transitioned into commercial.


Z, do you know what time it is?


It sounds like this is your —


The For Real Deal. All right, Ashley, this is the first deal you do as a real estate investor, whether it’s intentional or not intentional, so tell us about your first little house hack you did as much as you can remember. It sounds like this was back in 2009 but, yeah, tell us all about it. What did you buy, estimated price, all that good stuff and what you did with it and all that?


First deal was very, very successful, which I know a lot of people can’t say that so I don’t take that lightly. It was dumb luck, honestly. We purchased the property in 2009, this is at the start of the housing crash, we bought it as a short sale and we bought it with Obama’s First Time Homebuyer $8,000 Tax Credit, if you guys remember that. So we were able to kind of like stack in terms of buying property at a discount with someone else helping you pay for it so it was a cool setup. Then we took the someone else helping you pay for it to the next level and, as I mentioned before, my husband was a professional athlete, he was an ice hockey player, so what we did is we rented out the other rooms to his teammates to offset our expenses, not even offset, pay all of our expenses and then some, so we lived for free while he played because his teammates paid for the other rooms. We also purchased a property that we knew would be the team’s party spot and we did that intentionally so that when my husband left that team, we would not have a problem renting it out to other guys on the team. And the other thing we did is because we were in the same position as them in terms of not wanting to lock into a year lease on a property, it made it very competitive in terms of his teammates wanting to rent with us because we didn’t lock them into a year lease. We didn’t want to lock them in for a year lease because his teammates didn’t want to lock into a year lease, we were able to tap into the fact that it was more lucrative to rent from us because they could rent just for the season and then not rent during the offseason. And we didn’t want them to rent during the offseason because during the offseason was the highest time for short-term rentals. So, then, over the summer period, we were able to convert it into a short-term rental and we made hand over fist. So, the first year we netted $20,00 in 3 months, the second year $30,000 and the third year $40,000. Then we turned it into a long-term rental because one of the people who rented it short term was actually moving to the area and asked if they could rent from us. They rented from us for I think three years and then they made an offer to buy it from us. So that property did very, very well and that was just one of those situations where it really was, looking back on it, like a little bit of dumb luck. I know we were watching BiggerPockets and we were doing all of our research so we bought it right, but in terms of all of those different revenue streams that we can maximize the real estate value on, we didn’t go into it knowing that so that was an added benefit.


Yeah, it’s kind of crazy that you knew to do all this stuff, like house hack and Airbnb all before it was super cool when you heard about it on podcasts and in blogs and there were no books on it and all that. But even more so, I think it’s easy to be like, “Oh, yeah, you bought in 2009 so you just got lucky. I wish I could have bought in 2009,” but really, if you remember in 2009, everyone was talking about how real estate was a really bad thing to buy, you shouldn’t buy it. The media was like, “No, don’t buy real estate, don’t buy real estate,” and so it takes that little bit of courage, a little bit of knowledge and maybe you’re listening to the right people at the right time to actually buy that and, of course, it’s like what Warren Buffett says, be greedy when others are fearful and fearful when others are greedy so you were greedy when others were fearful and you got paid out perfectly for that. And I think like as we head into potentially another recession and maybe the housing market does crash again, like people out there, this is the time that we’ve been waiting for since 2009 so people buying now could have similar results as to what you had in 2009, I just want to point that out. And so do you remember, Ashley, what you purchased it for and what you sold it for?


I think we purchased it for like — I want to say like 120 maybe, 130, around there if I remember correctly and I think we sold it for like 160 so we didn’t make like a lot of money on the purchase and sale, where we made money was on the cash flow because we should have kept it as a short-term rental because, honestly, it could have short-term rented all year round 12 months, but, like I said, we weren’t focused on it. We didn’t, shockingly, we’re like making all this money from it and not even acknowledging it as a good investment. I look back on it and the fact that we got in the short-term rental game before it was popular is wild to me that we didn’t pursue that route. Like it was so easy, it was so much money, and it was something we could do full time.

The fact that we didn’t even think to scale it, it’s just mind blowing to me knowing what I know today. Click To Tweet

Yeah, and can I ask where this is located?


Hershey, Pennsylvania.


Okay, awesome. Well, Zeona, do you have anything to add or anything like that before we head on to maybe deal number two?


No, I think it’s great. I mean, I’m just blown away too that, I don’t know, it just seems like it could have been such an amazing opportunity but now knowing just even a little bit of value, I know that you’ve recovered so it’s fine. You found your own asset class and it’s great. But going from this one house hack, what made you want to continue? Was it that you fully sold this house and you needed a new place or were you still renting it and you were like, “Okay, we don’t wanna live with all the guys anymore”?


My husband got traded — he didn’t get traded, his contract ended with that team and then he signed a new contract somewhere else. So we moved but we kept running into the guys even when we weren’t there, so looking back on it, we were just in a situation where we didn’t need to buy another house. I mean, there are a lot of good things about when he was playing professionally, but one of them is, depending on the team, oftentimes, they take care of your housing for you, for those nine months, other teams don’t, but it’s kind of assumed you’re just going to rent in those markets so we just went to another market and we actually rented in that market, but, looking back, every time he played somewhere else, we could have just bought another house and then run into the guys.


Yeah, I was going to say, it’s so perfect. It’s almost like being in the military, how every time you get transferred, you can really just buy a house and if you do that a few times, it’s like an easier house hack almost because sometimes it’s not even a full year and then you have the perfect excuse that you can actually qualify for another loan. So, missed opportunity but it still sounds like you guys did some of it. So what was the house number two?


They were like our houses and then we would rent out other rooms. We actually house hacked.

People say you can’t house hack in different stages of your life. Click To Tweet

We house hacked up until a year ago, our entire relationship, so we house hack through dating, through engagement, through marriage, through kids, through full gut renovation. We’ve house hacked with different people but we’ve house hacked all along the way so that really was like our next investment but, honestly, in terms of changing investment profile, the next big change we made was we went into flipping. So, I left pharma in 2013 or ’14 and I approached my father, who’s a general contractor, about partnering to flip houses together. So I was living in Europe and Russia at the time because my husband’s career took us over there and you pretty much can do almost everything from afar in flipping so I found the houses, I ran the numbers, I did the design, I scheduled contractors, I ordered materials, and then my dad, he did the permit applications. He called it adult daycare, which means he made sure that the contractor showed up and did their work according to what we wanted. So he served as boots on the ground. And we grew that business quite successfully and targeted older full-gut high-end rehabs.


So where was that? Where was your family or where was your dad at that time?


We live in the suburbs of Philadelphia so that’s where I was born and raised and still live there today. There’s an area that stretches from Philadelphia to Lancaster and it’s called the Main Line because there’s a main road that connects these two cities and houses that are on this line tend to be early 1900s homes, they tend to be homes that — Philadelphia used to be the capital of the country, capital of the state, and very wealthy, prominent people would live in Philadelphia and then have their summer homes on the Main Line so on the outskirts of Philadelphia. So these homes have a lot of history. They’re exquisite. They’re very, very incredible houses. My dad is very well versed in old historic homes and full-gut rehabs so we were able to niche in to that market and also be very competitive buying most importantly, because most flippers focus on cupcake quick rehabs that are low price point, like $300,000 or less.


So I love this. I feel like this is a moment to just talk about mindset because your dad had been it sounds like a contractor forever but it took him having you from the outside perspective say, “Hey, let’s do this flipping thing,” even though he had all the knowledge and all the ability to just do that, and it’s interesting how a lot of people that are in contracting work or some kind of builder, this is like an example with my sister’s husband’s family, they can do anything with homes but they don’t have this know-how to create a business in flipping to take that next step. There’s a lot of fear there. So what did you have to overcome with your dad to get him to say yes to this project?


My dad always says that, and I do believe him on this, that he believes in me. He knows that I’m a very driven person so he knows that when I do something, I just won’t let it fail. I’ll figure out a way. I’m a grinder. So, in terms of getting him to at least take the initial step, he had comfort in doing that. I think the challenges that I had to overcome with my dad is that, on the first house, even though I know construction, I didn’t at the time. So this is back in 2014. I didn’t know how to renovate a full gut. I mean, literally full gut, like everything. And we did a two-story addition. So, it’s not a matter of just the full gut, it was the full gut plus a two-story addition, I didn’t know the orders of operation so to kind of put it in perspective, on the first deal we did, we made $66,000. It took us — which is very good, because, at that time, I think 95 percent of flippers, first-time flippers, lose money on their first deal, and of that 5 percent, it’s like 90 percent only make $5,000, some crazy statistic, so my dad is ecstatic we made $66,000 and it took us a year from I call it acquisition to close but it’s from when you purchased it to when you sell it, and nine and a half months of rehab and then the lead time to get to sale. My dad was ecstatic. He was pumped at, we split it 50/50 so he was pumped it $33,000 gross and I was like so pissed off. I was like, “This is a failing business. What are we doing?” And he was like, “What are you talking about?”

And I said, “Dad, can you live off at $33,000 a year? Because I certainly know I can’t.” And he said, “No, I can’t,” and I go, “That’s why it’s a failure.” Click To Tweet

It’s a failure because it’s not sustainable so we need to figure out how to make this sustainable. So, a year to date, once we closed that property, we got another property and it was a larger house, a larger scope, a larger two-story addition, ironically, it also had a two-story addition, and a larger house and we did it in nine and a half weeks and we made over $100,000 gross. It was like $115,000 gross or something like that. And I said, “Dad, this is how you do it.” We bought the house in September, we sold it in November. I was like, “This is sustainable. This is scalable.” And it’s all because my dad had the wherewithal and the knowledge and the experience on the construction side but I had the management, the system-oriented mindset in terms of how do I systematize it, how do we automate it, how do we delegate it to make it a business and not a hobby. From that moment forward, even when we first started, my dad’s always relied on me for insight because he always says, “I work in the business, you work on the business,” kind of responsibilities but, that to him, he was like, “All right, I’m all in. Whatever you tell me to do, I’m going to do because you just proved to me that this can be extremely lucrative.”


All right, I’m going to just pause here for a second and put in our ad for today. It seems like our theme has been about mindset a lot. And I think that’s about who you surround yourself with and so, if you guys don’t know, I have a Facebook group called Airbnb Investing, just search those words, and we help each other in there. So I do custom webinars in there or, I don’t know if custom is the right word but just weekly webinars. We answer everybody’s questions. There’s just a really supportive group. And so that’s completely free. Go check out Airbnb Investing. All right, back to your show, Ashley. So, what is the theme here? You’re like this business driver and you’re just like keeping this going, but it sounds like you left flipping and so what was the thing that said, “Hey, maybe this is not forever for you”?


I think two things — actually, it might be three things really. One was I, personality wise, like to be intellectually stimulated. I always have to be challenged mentally and flipping just doesn’t do it for me. I love working with my dad, I love before and afters, but it’s not intellectually stimulating. I don’t know how else to put it, it’s not challenging and my brain needs to always be at work and I find it very redundant and boring and even if you can make a lot of money on it, it doesn’t interest me as much as commercial real estate because I find commercial real estate to be much more challenging. That’s number one. Number two is from a market standpoint, where we were in the market cycle, I didn’t think flipping had a lot of runway left in terms of where we were headed. I think COVID did some crazy things. It made it really great at first but then, now, arguably, I don’t know if flipping is the best thing to be doing right now, especially with interest rates and the loans that people were refinancing into, I think that’s going to be really challenging and then what loan they get into. I think it’ll come back around shortly here but I definitely, pre-COVID, I didn’t like where things were heading in the market. And then third thing is, at the end of the day, it’s not a wealth vehicle, it’s another job, and if you’re looking to grow wealth, flipping houses is not the answer.

You can use it as a driver to help you grow wealth, you can take the surges of cash and then reinvest those elsewhere and that can be building your wealth, but, at the end of the, day flipping is another job. Click To Tweet

It doesn’t have tax advantages. It’s highly taxed, actually. It has the opposite effect of growing well. So, to me, it didn’t align with our overall strategy, our family strategy.


It sounds like from 2014 to 2019, you were doing the house flipping, you probably build a pretty scalable business. What made you decide on this specific commercial investing and what did you end up deciding? Because I know there’s mobile home parks, there’s industrial, there’s so many different avenues you could take.


That’s a great question and I think it speaks to how analytical my husband and I are because he retired in 2017. From December of 2017 through March of 2018, we did like almost like a high school debate class so we started with 22 different asset classes we would be interested in in real estate and every single weekend, we debated on which one was the right one for us and we landed on multifamily. It doesn’t mean that it’s the best one for everyone, it just means that it’s the best one for what aligns with our family, our skill set, where we believe the market’s headed, how we want to grow our wealth, and what we want our future to look like. So, multifamily, for me, there are a lot of reasons why we invest in multifamily. Number one, everyone needs a place to stay. Number two, it typically is a hedge against inflation. Number three, if you look at the past recessions and multifamily rental performance typically stays the same, if not goes up during recessions just because there is such a lack of home purchases at that time which forces people into a situation in which they need to rent. That’s historically.

If you look at what’s going on today, we have more renters by choice versus renters by necessity, which is kind of a change in the market which is why I think the BTR communities are such a fad right now because people want to play off the fact that renters by necessity is growing. So, there’s a lot of ways in which multifamily can be seen. And I mean, if you just look at basic economics with supply and demand, there’s such a shortage of housing across the country, especially in major MSAs. So, those are some top level reasons we like multifamily.


So would you recommend somebody new getting into multifamily? And if they wanted to, where could they start? Because we’re kind of towards the end of our show and I imagine you have some tidbits for the newbies.


Yeah. I mean, personally, I think everyone should be in a position where they are collecting rent from something, whether it be multifamily or a laundromat or something. But multifamily I think is a great investment vehicle. There’s a lot of different ways you can get into it. If you want to be a passive investor, if you’re like where I was when I first started my career where I was so focused on corporate America and I didn’t have time to focus on real estate, you can align yourself with different operators and passively invest in different real estate offerings, both accredited and non-accredited depending on the investment. You can also, if you’re more of an active mindset, you want to be actively involved in real estate and multifamily, you don’t have to do it in the scale that I’m doing it at. You can buy a duplex or a quad and be under a residential loan or you can go five units and up, you can be under a commercial loan.

There’s just a lot of different ways you can get in the game. But if you’re listening and you’re like, “I hate real estate, I hate multifamily,” just because you hate it doesn’t mean that it’s not a good investment and you can align with other people… Click To Tweet

Clearly, I love it but there are other investments that I invest in. I hate that, like I would never be able to do that asset class but I believe in that asset class so I invest in it. So, you don’t always have to be an active investor.


Yeah, I think it’s really important to take the emotions out of investing, and so you don’t buy a place because it looks cute, you don’t buy a place — you’re investing literally, if you’re investing, it is to make more money and to have the highest return on investment as you possibly can actually. Let’s talk real quick about what did it look like for your first multifamily deal and what were some of the feelings you were having as you kind of got into that bigger space and dealing with more money and investors and just numbers are probably ten times the size, let’s get into that a little bit.


Shockingly, the numbers didn’t intimidate me, the operations intimidated me. So, when we are purchasing, first of all, I did it with a partner, a partnership group, a company, and I ran asset and construction management, we raised about a little under $3 million to acquire the property and that was a little bit intimidating but that wasn’t my role so I didn’t have the pressure of like, “Oh, well, if we don’t raise this money, we can’t do this deal.” They definitely did and I saw that firsthand and I learned a lot from, honestly, their mistakes and things they did do right and things they didn’t do right so that was helpful to see as kind of an outsider. But then in terms of asset and construction management, the thing with me was that I had never done a duplex, I had never done a quad, I had never done a 20 unit or a 40 unit, I had never done any multifamily, and, all of a sudden, my first deal was 124 units. So, similar to how crazy I was in pharma, I spent hundreds and thousands of hours digesting anything and everything that I could possibly find on asset and construction management all the way down to property management. I spent thousands of hours with my regional property manager at the time, who’s now, no joke, is my best friend and she’s since gone off and started her own company and she runs all of our properties. But I didn’t even know what I didn’t know, that was the scariest part about it. I have never in my entire life learned more about a subject than in the first year and a half of multifamily, learning about multifamily. But, to that point, and I’ve always said, you know how like you come across people in life and you feel like you’re on the same path as them and everything just comes so easy for them, they get the easiest projects and they get the easiest, like they’re constantly winning and winning and winning and you’re winning with them but you’re struggling the whole time, like you have the hardest properties, you have the hardest tenants, you have the hardest, like everything is so hard but you guys are kind of growing at the same pace. I’ve always kind of had that, especially in real estate, but one thing I can say about real estate is that in my first year and a half, two years of real estate, I know for a fact that I experienced more than people I was looking up to who had been in the business for 10, 15, 20 years. And I know that because when I would have conversations with them, they couldn’t even talk about multifamily at the level I could speak to it at and they kept looking at me and they’re like, “Are you sure you’ve only been in this for like a year or two years? How do you know all this stuff?” and it’s just because I was tested. I was tested with gas leaks. I was tested with a permanent building that burned to the ground while we were under contract and we had to rebuild. I was tested with lawsuits. I was tested with dealing with the city over ordinance issues. I was tested with lender issues. I was tested with investor issues. Literally, I think I’ve been tested with every single thing you could possibly be tested with owning multifamily and I think that has put me in the position that I’m at today where I don’t fear any aspects of multifamily because I just see it as I don’t know the information yet but I will be able to learn it, I will be able to figure out a way to make this successful and come out ahead for our investors, because the most important thing to me is protecting our investors.


Wow, you’re like “Go get them” is so inspiring. Well, we need to transition to the final part of our show. So, before we do that, do you have any final words of wisdom for people that have been listening today?


I think if you’re inspired by anything that I’ve said, I just would recommend that you take action and you set a date in which you take action. I think a lot of people say they’re going to do it but then life gets in the way. And life’s always in the way. I mean, when was it a good time to go back and get your master’s? When was it a good time to have children? The answer is it’s never a good time. It’s never a good time to do any of those things, but you never regret it. And I’m telling you, you’ll never regret taking action.

As long as you put the knowledge behind it and align yourself with knowledgeable people, you’ll be grateful for the opportunities that real estate can provide. Click To Tweet

Ashley, I just love that. I love the whole point of just like taking action and it sounds like you’re not afraid to educate yourself to the max as well. And it sounds like you take action and you educate yourself as you go, which I think is extremely important too, so that you’re not getting into that analysis by paralysis phase and I want people like here listening, Ashley is a super successful real estate investor. She’s got — how many units do you have, Ashley? I don’t think we got to that.


It’s over 700. We’ve had more than that but we’ve sold a few properties. But today, it’s over — I’m not a big unit count person so I intentionally not remember it but it’s over 700.


Right, but, the point being, it’s obviously you’ve got hundreds and you’ve probably had at least at a point a thousand plus units and you don’t get there overnight, and so if you’re listening to this doing your first or second deal, remember that Ashley started with a house hack which she was renting out to a bunch of her husband’s teammates on his hockey team and then got a couple of those and then just kept learning and learning and learning and growing and growing and ten years later, she’s doing big multifamily stuff. And so make sure you’re just not comparing your chapter 1 to Ashley’s chapter 10 because I think everyone listening to this podcast, if you do desire to get into multifamily, whether it’s next year or five years from now, you absolutely can get there and so I just want to make sure that that point is clear, because I think comparison is a really easy thing to do. Okay, Z, I think that’s my — I’m going to get off my soapbox and I think we’re ready for The Final Four. Okay, Z, kick us off.


All right, Ashley, what are you reading right now?


I am actually writing a book right now so I have very little time to read except for the research that I’m doing for my book, but I was reading — what was the last book I read? Actually, the last book I read was Jason Drees’s Do the Impossible, which is a very interesting book. Very, very interesting. I would highly recommend it.




Yeah, I’ve heard really good things about that. I haven’t gotten to it yet. What book are you writing? Can you tell us?


Oh, it is about multifamily.


Get out of here.


Who would have guessed?


Well, my last one was about real estate in general so it is about multifamily but it’s more on trends than how to do multifamily, I guess that’s all I will say at this point.


Okay, so sounds very research intensive. So I take it that’s what you’re doing a lot of.


It’s very research intensive. That’s why I’m not reading.


That’s why you’re not reading, yeah. Just reading analyst reports.


Just reading constant reports. It’s a lot.


Yeah. Okay, Ashley, second question, what is the best piece of advice you’ve ever received?


Don’t mistake my kindness for weakness. My mom says it all the time.


Oh, that sounds like a mom quote. I love that.


Sounds really intense.


I love that. Okay. I’m taking that one.


Oh, I know. I want to start saying that. I just feel like there’s certain things I want to save up for like later in my life because it’ll just be like more badass when you’re like that older lady.


Yeah, store that in the bag.


Right. Okay, question number three. What is your why?


My family. Everything I do is for my family and building generational wealth. So it’s not about the wealth we can build today, it’s the wealth we can build for the future for my family.


Awesome. I love that. Ashley, last question, would you rather have no nose or no arms and why?


No nose or no — like nose? Like on your face? Or no arms? Oh, this is a curveball. Let me think about this because I am someone who, I’ve said before that I have to kind of process this. No nose, so then I wouldn’t be able to smell. But then smell is also tied to taste so I also wouldn’t be able to taste. Or no arms. You know what, I actually might go with no arms because there are a lot of different prosthetics now that actually sync to your neurons in your brain and they’ll send signals to your prosthetic arms and you can still work your arms and the fingers and stuff like that so it’s like a whole prosthetic so I’m going to go with no arms.


Okay, that’s sneaky. That’s sneaky.


Because that’s something that I can like compensate.


This is like a smart person’s answer.


Yeah, Ashley, that is that is definitely way more analytical than I ever expected. Yeah, I think you’re definitely the smartest person in this room at this point. At least with me. You might be in competition with Z. Okay, so you’re keeping your nose, ditching the arms, got it.


I’m keeping my nose.


Okay, Ashley, where can people find out more about you?


You can follow me on Instagram at @badashinvestor. You can, if you’re interested in passive investing, you can find — J. Scott is my partner so J and I have a company called Bar Down Investments and we also have a coaching program if you want to actively invest in multifamily and that is Apartment Addicts so either bardowninvestments.com for passive investing or apartmentaddicts.com for active investing and learning how to find, fund, and run multifamily apartments.


I love that. There’s a power duo right there. J. Scott is like one of my favorite people in real estate. He’s just such a smart guy. You guys must be a great team. And, yeah, definitely check out Ashley’s Instagram and if you’re interested at all in multifamily Bar Down and Apartment Addicts. Check it out. Ashley, thanks so much for coming on the show. It was so good to have you on and so good to enlighten us with all of your different real estate endeavors and it’s just amazing to hear your story kind of how much you’ve grown in just ten or so years. I think that’s just so inspirational to a lot of people. So thanks so much for coming on and we’ll chat soon.


Sounds great. Thank you so much again.





And that was Ashley Wilson. Z, what did you think about Miss Ash?


Bad Ash.


Bad Ash.


And that’s her Instagram handle. I’ve met Ashley a few times. I think she’s super inspiring. She’s usually at conferences speaking on the women’s panels just because she’s done so much in real estate, she’s done so much in business, and she’s a powerhouse woman. I wanted to mention the name of her book. It’s called The Only Woman in the Room. That’s the book she has out currently and that was — I think it was published by Investor which is kind of like — I think they’ve made an attempt to do book publishing kind of like BiggerPockets does, but, yeah, go check out that book because it is a compilation of a bunch of women investors talking about different ways that women are often kind of like the minority out in real estate and it’s so amazing to see women really succeeding in this. I think it’s super inspiring, I think —


Z, are you in that book?


I’m not.




That would have been really funny. I’m like this is the most amazing book and then I’m in it, by the way. No, that wasn’t what I was leading up to.


I’m the first one, I was waiting for your plug. She needs to update it and put you in there.


No, yeah, well, I’ll tell her that.


Yeah, you tell her that. Let’s see what she says.


What did you think, Craig?


I think Ashley’s story is just — it’s like the perfect real estate story. You start off with a house hack, kind of test out the waters, show the wealth, learn without significant dollars at risk. And then as you learn and grow, I feel like you always gravitate towards a specific field and so like, Zeona, you’re doing the medium-term rentals and you’ve really enjoyed that space and that’s where you’re growing and then you’re finding ways to scale there. She found a love in commercial real estate and so her and her husband sat down, did a big analysis, and they found out that multifamily is where they wanted to go and so then she just dug deep into that, started learning, and now she’s got over 700 plus units, partnered with a very, I guess, would say prestigious person in J. Scott, and she’s just absolutely — she’s crushing it and so there is no reason, like Ashley is no different — you heard her whole story from childhood to today. She’s no different than any of us. She’s no different than you listening to this. And so, again, she’s just maybe a little bit further along in her story than you are so just stick to your story, get your first, second, third house hack and then you’ll see that you’ll start to grow in different endeavors.


Yes, but until that time, if you liked this episode, go check out Ashley’s podcast with J. Scott but also leave us a rating or review, share this episode with somebody you love and care about, and come back to us week after week because we love talking to you.


Yeah. And so we will see you guys all next week.




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