From Madison Avenue to Billions in Multifamily with Joe Fairless - EP38

In this episode of The Wealth Clock, host Steven Weinstock sits down with real estate titan Joe Fairless, co-founder of Ashcroft Capital. Steven admits to a bit of "fanboy" jitters as he welcomes the man behind one of the longest-running real estate podcasts in history, the Best Ever CRE Show.

The duo discovers a striking parallel in their backgrounds: both started their careers in the high-stakes world of New York City advertising on Madison Avenue. Joe shares his journey of living frugally in "no-living-room" apartments to save for his first single-family rentals in Texas, while Steven recounts his early days selling digital banner ads in the pre-Google era of 1998.

Key highlights of the conversation include:

• The Pivot: How Joe transitioned from a $30k-a-year junior project manager to controlling over 14,000 multifamily units.
• The First Deal: Joe’s initial foray into the Dallas market and the hard lessons learned from remote renovations and property management "brand names."
• Creative Financing: Steven and Joe discuss the power of master leases and seller carries in scaling a portfolio.
• Market Insights: Joe breaks down why he believes Atlanta will lead the Sunbelt recovery, followed closely by Dallas-Fort Worth and Orlando.
• Life Beyond the Deal: Joe shares his unique "personal challenges" for the year, including primitive fire-making, carving chess pieces, and walking 100,000 steps in a single day.

About the Guest: Joe Fairless

Joe Fairless is the co-founder of Ashcroft Capital, a firm that has acquired over $5 billion in assets. He is also the author of several best-selling books on real estate investing and the host of the Best Real Estate Investing Advice Ever show.

Connect with Joe:

• Website: AshcroftCapital.com
• LinkedIn: Joe Fairless
• Podcast: Best Ever CRE Show

About the Host: Steven Weinstock

Steven Weinstock is a real estate investor with over 25 years of experience ranging from single-family homes to large-scale multifamily syndications. He is the founder of a mortgage fund focusing on private lending and short-duration, first-lien secured loans.

Connect with Steven:

• Website: The Wealth Clock (or your specific fund site)
• Sponsor: CableNOI.com – Helping multifamily owners unlock hidden revenue.

🎙 About Steven Weinstock
Steven Weinstock is a real estate investor and founder of WeCapital and the Goethals Capital Fund. Since 2001, he has built a diverse portfolio of residential and multifamily assets while helping investors access passive income through strategic real estate opportunities. On this podcast, he shares real-world insights on investing, capital raising, and what it really takes to build and scale in today’s market.

📩 Want to invest or get in touch?
Visit: www.WeCapitalX.com

📱 Connect with Steven:
LinkedIn: www.linkedin.com/in/stevenweinstock1

Instagram: https://www.instagram.com/wecapitalx/
YouTube: https://www.youtube.com/@TheWealthClockPodcast

Transcript

0:00

Hi and welcome back to the wealth clock with Stephen Weinstock. I'm your host. I've been investing in real estate for about 25 years. Over that time, I've purchased everything from a small single family to larger multifamily properties. Today, my focus is building scalable real estate investments, creating opportunities where investors can participate in real estate in a more passive way. One of the areas we focus on is private lending through real estate secure loans. Our mortgage fund provides a short duration first position loans, in and out usually about 12 months, interest rates anywhere from 10 to 15% and typically 65 % loan to value. I do have a sponsor, Cable NOI. Cable NOI helps multifamily property owners unlock hidden revenue from their buildings. by negotiating bulk cable internet agreements with major providers. In many cases, cable company pays owners an upfront per door fee and provides ongoing revenue, all without tenants needing to change their plans or owners to handle any kind of billing or anything like that. If you own an apartment building with 20 units or more, simply visit cablenoi.com. Plug in your address. It's free. It's always free. So I'll get back to you about two weeks later, letting you know if there's an offer on your property. Today's guest, I'm a little... nervous to have him on, even though this is episode, I don't know, 39. You'll see it in the show notes. His name is Joe Fearless. ah He is famous, so it's hard for me to stick to my script that I have in front of me, so I'm a little jittery over here. He is the co-founder of Ashcroft Capital, a multifamily investment firm responsible for billions of dollars. and apartments assets across the United States. He is also the host of the best ever CRE show. Famous podcasts. If you're listening to this, you've probably heard of that one. Wide recognized as one of the longest running podcasts in the real estate investing space. Thousands of interviews, operators, investors across the industry. Joe, you started your career in New York. Am I correct on that? that? You are correct, I sure did. Alright, before you were in real estate, you were in advertising. That's right, yep, my major at Texas Tech, so I'm from Texas originally, born in Michigan, but from Texas Tech originally, was advertising with English minor. And my first job out of school out of Lubbock, Texas was in New York City. I wanted to be in New York to compete with the best of the best in advertising. So I went to Matt. I worked on Madison Avenue on 51st and Madison. We the building overlooked St. Patrick's Cathedral and it was right by I think there's a Nike store right across the street. Also, big old Nike store. So I worked in advertising for my first eight or nine years in New York. oh I have a little background in that career also. So I started buying real estate. I started buying real estate in 2001, but in 1998, I was working on Madison Avenue and 27th Street, um right near Eastern New York Life Building, at least that's what I saw in the background at the time. I think it's no longer called the New York Life Building. And I spent about three years. working on online advertising. is back then. So this is pre-Google. This is... yeah, oh yeah. So this is pre-Google. We were working with companies like DoubleClick, which eventually got bought by Google. We worked with 24-7, I think it was called 24-7 Media. They were selling banner ads on homepages of Yahoo, Excite, Lycos, AltaVista, GeoCities. And I'm just trying to remember, this is a web... of pre-2.0. Oh yeah. yeah. This one, Netscape was still around. And yeah. asking people for their email address. You were considered a nerd weirdo instead of just asking for their phone number. But I definitely remember those days. uh How do you pivot after, I guess, eight years in real estate to real estate? sorry, in advertising to real estate. estate. Yeah, was gradual. It was gradual. And then there was just an abrupt... abrupt shift. the gradual part was I was buying single family homes. my salary starting out in New York was making $30,000 as a junior project manager at the advertising agency. I as I climbed the corporate ladder. I kept my living expenses really low especially for New York City standards and I always had a roommate I My my apartment was really tiny. It didn't have a living room. I Was a two-bedroom, but that's about it. It was two bedrooms a hallway a bathroom and a Stove and a dorm style fridge. There's no living room. It's just just kind of like a from the bedrooms to the bathroom, where a stove in between. So I was made fun of a lot by my friends saying, hey man, you're living like a college kid, you're seven, eight years out of school, but what I was doing is as I was climbing the corporate ladder and advertising, I was saving my money. and I would save it to buy single-family homes. And I bought my first one in Dallas, in Duncanville in 2009 for $76,000. Then I bought another in Fort Worth and another in Arlington and another in, I think, Arlington. And I ended up with four and along the way my friends and coworkers were asking me, well how are you doing this? You're working these crazy hours in advertising. How do you do it? And I said, well, I have a system. And so I started teaching people on the weekends how to do it. I would have a class how to do it and eventually first like. Two people came, then eventually up to 12 people came. I think that was the max that came to the class, but I would do it consistently. And I would teach people how to live in New York City, but invest where the numbers make sense. So, yeah. Where in New York were you living, just out of personal curiosity? I lived one year in East Flatbush, Brooklyn. Church in Nostrand were the cross streets. And I was about two minutes away from the Church Avenue 2 line, the stop on the 2 line. And then for nine years I lived in East Village between First Avenue and Avenue A on 9th Street right by Tompkins Square Park. Got it. I have a, you my audience knows this, but I'm born and raised in Brooklyn and I'm recording right now here from Brooklyn, not too far from where you were. I am right now in the Mill Basin Marine Park area, which is, guess, South Brooklyn, but born raised, but I don't invest in New York either. So, uh you know, I'm going to ask how you found Dallas for your first property. But my first property as I was working a corporate job. was about an hour drive outside. It was Trenton, New Jersey. It was a single family home. Thirty two thousand, thirty two five. I put 10 percent down. This is 2001. So I 10 percent down. I was able to get an 80 percent loan and then at the same time of closing a 10 percent loan. So I had a first and second. both by banks. So this wasn't some sort of hard money or anything like that. I put down about, about 5500 total for down payment and closing costs. And my goal was to own just one and you know, pay it off over 30 years. And when it's time to retire, when it's time to retire, have another bonus uh 401k. And after collecting rent for two months, three months, the numbers really started clicking. and I started looking at the amortization schedule and, you know, the few dollars a month I was making. realizing that my cash flow would really increase a lot. Specifically when I paid off that small second wing because it was a big chunk. That wasn't advertised over 30 years, I that was over five years. So I had a larger payment, but I knew as soon as that's paid off, I'm really in the money. And I said to myself, one at a second, one at a third. And during that time, it was little easier to buy. This is a pre-subprime. Like you said, he got into it in 2009. But, so, 01 to 07 was very, I hate to use the words easy, but it was very easy to buy, one to fours. And... And just about all my debt was always fixed for the most part. I didn't have any of those arms, you know, adjustables that a lot of people got into trouble with in 08. So it was very good to me. You know, I I maximized my luck during a good time. So how'd you find Dallas? You work in New York, you're not from New York, but guess investing in New York is too hard. uh well, I'm curious do you still own that first property in Trenton property I happened not to own, but the second and third I still own, and I still own a bunch in that area. Even though I haven't bought in that area in over 10 years, uh maybe even more, I still own a few. Some of them are sentimental. Some of them I've been able to refine, pull out, and I haven't really felt the need to sell it. Don't get me wrong, I've sold plenty of stuff over the years, usually just for... lifestyle. I started off buying when I was a kid, so to speak. Now I'm married with seven kids. But every time I sell something and I drive by, like a year or two later, I get upset. Hey, it's worth more than I sold before. And I really went through the hassle of putting it together and buying. Maybe I could have just, you know, refinanced them, but, uh you know, it's just the way it goes sometimes. Did I hear you had seven kids? Yeah, I have six boys, one girl. My oldest is 19 and a half. He's in college in the city. And my youngest is first grade. And the same question I get all the time after I say that. So I'll just preempt with an answer. Yes, it's with the same wife. Yes. I wasn't going to ask that, but that's funny. Well, you asked about how I got involved with the deals in Texas. Well, was my sister was a real estate agent in DFW. I was from Fort Worth. So it was, I guess, turnkey for you, at least properties? They were except for the fourth so I I got more creative on each of the as I kept going so the first one I put 20 % down I think 76 yeah, I think I put 20 % down. Yes, I remember putting percent down because all I know is about $20,000 and then the second one I put 10 % down through a loan program called a Home Path loan. The third one I bought all cash but then I did a cash out refinance shortly after and got I think most most of my money back or maybe all of my money back I don't quite remember. Then the fourth one I bought with a line of credit that I had from a credit union I bought it from a wholesaler and that was the non turnkey one that turned into just a Mistake on my part Because the first three were turnkeys great. I'm remote everything works the fourth one. I had to hire a contractor and it was a family friend, but Turns out the family friend, were within their family, they were on the outs. There was some dynamic there that I didn't know about. Anyway, the property didn't get renovated as quickly as I wanted. And I ended up selling that fourth one for about what I had put into it. So I learned not to do, for me, to do renovations remotely, because that's more of a hands-on thing. What were some of the first bumps you had in first two or three properties that you bought? Is that what it was? Oh, that was one. Another was property management. The very first house that I bought, I hired a property management, a Century 21 property management group. So they were, you know, they had the brand name, but they were terrible, absolutely terrible, that group. And I ended up... creating a website for the house and marketing the website on Craigslist and you're just trying to get the thing rented and then eventually found a really good property management company in DFW and again this is... uh however many years ago, this is like 16 years ago, so I don't even know if they're around anymore, because I don't buy single family homes. But they were phenomenal. So it was finding the right property management company and being more hands on when I needed to. At first I thought it was just, buy the house and the management company leases it and then that's it. there were more twists and turns. I also realized that when someone would move out, I'd make 250 bucks a month, but when there was a move out that cost $3,000 to get it moving ready, and that would wipe away the profits for a year or two. I saw the importance of keeping the residents in the homes for the long run, even if it doesn't, even if it's slightly below market rent, because I still profit and I pay down the principal on the loan and times on my side. How did you, how long were you in this space before you pivoted to multifamily? From 2009 to 2013. And then 2013, I got a 168 unit property because I was teaching that class on single family homes and a boss of mine at the time, or a former boss at the time, he said, this is good, but if you ever do something larger, let me know. So I realized that I had customers before I had a product. had... potential investors before I had actual deal. So then I ended up getting through a master lease with option to purchase, which is a whole creative financing structure, a 168 unit in Cincinnati. Got it, yeah, creative financing was and is my best friend and it's how I was able to buy lots of one to fours and I even took some of that skill uh or creative ideas into the multifamily space as well. uh I've kept the owners, sellers in the deal with some sort of creative finance component to it. uh When you were giving these classes when you first started, this was live, I assume, this was pre-Zoom. Yes, it's pre-Zoom, yeah, this is in person at co-working spaces. I just found, well, I mean... And you were charting for these classes, I assume? Maybe maybe $50. I don't I it was nominal Yeah, well, I mean and to save money I was I was You know, I was I was babysitting on the side after college in New York City I was you know, I was manning man mail mail nanny where I would go and and On the weekends, I would do that like on Saturdays or Sundays So I was it wasn't just to keep the road after that it was to tuck money away and save and then put towards real estate And I think around 2014 or so Back then it was tougher than it is for all these new podcasters to come out with all the tech out there. And back then it was a new space. uh it was really revolutionary back then, especially. uh had to teach myself how to edit. I had to teach myself Audacity, which is an editing software. And yeah, I had to start it from scratch. One podcast was helpful and that was Entrepreneur on Fire, John Lee Dumas. I researched... all the stuff that they did. so there was a model and there were some other real estate podcasts out there. I don't know if they're still doing it now, but at the time there, wasn't anything like Like now you don't even have to have human beings to have a podcast. You just upload a script or upload a document and then a bunch of robots talk to each other that sound like humans and there's a podcast. But nothing replaces what's going on right now between us where I'm learning about you you're learning about me, we're building some rapport, we're getting to know each other. I mean that's the stuff that people... are going to miss out on if they just do the robot version of things and you lose a soul of what it's like to be a human on this earth. And I'm all about AI and helping it do and having it do things that are repeatable and are more systematic. But there's also the flip side to that that I think we've got to be careful of and be intentional about continuing with build relationships. Yes, you know, I use AI a lot or more and more, you know, just like everybody else. Originally, it was just to help me write some emails. And then it was instead of searching YouTube on how to find the feature and some sort of property management software, I would ask Jatch GPT. But I started playing around more and started using learning about automations to help with just some, you know, three minute tasks that I have to do two or three times a day. And to have those automated, they used to be, hey, it's three minutes, you know, could do it for my phone. But now it's, you know, it's, it's automated. And yes, it's just three minutes, but it's, you know, three times a day for a week, you know, comes out to, you know, a billion hours a year or whatever. is. And to save that time, it's really phenomenal. And, you know, I always thought of myself as this tech guy, you know, I'm 47, but hey, I was selling internet ads in 1998 over here. And I had an Android phone before, or an iPhone, whatever. you know, early on or had the Palm Trio phone, obviously a Blackberry and all that. And I was texting early, you know, I remember sending people a text with my flip phone and they would be like, hey, how do you send me? You know, they call me up. Hey, how do you send me that message? You know, I remember that. But tell me about Ash Grove Capitals. This is your company, your vehicle to buy multifamily. I know you specialize in value add, if I'm not mistaken. What are some markets that you're investing in? Yep, so Ashcroft is, as you mentioned, a multifamily investment firm. We buy in the Sunbelt. We've got about 14,000 units right now that we're the general partner on. And we buy in, as I mentioned, the Sunbelt, but more specifically Dallas, Fort Worth, Tampa, Orlando, Jacksonville. Chapel Hill, North Carolina and Atlanta, Georgia. Those are the markets that we're currently in. From the four markets you just mentioned now, it's March 4th as we record this, from those four markets, which one, and again, real estate is so local, you can have the building across the street from each other, one's a rock star and one is horrible, and for that reason, you could be trying to do the same thing with both. um of these markets from these four that you're just not loving as much as maybe... a year ago or two years ago? Well, every market in the Sun Belt has slowed down and either had flat or negative rent growth, generally speaking, in the Sun Belt. Obviously, there's always outliers, but generally, that's a fair assessment of the Sun Belt. So over the last two, three years, you they've all been a challenge with negative or flat rent growth, which is brought on by the amount of supply that has come into the Sun Belt over the last two to three years from the lower interest rates before. But I'd say the markets that are now a prime to recover, I'd say out of all those markets, Atlanta would be the one that from what I've read and what we're seeing is gonna be the leader in the recovery from the markets that I've mentioned. I think DFW is right behind them and then probably Orlando. Yeah, we're we're we only have one property in Chapel Hill and it's it's it's got some student housing cycle for leasing. So that's a bit of an anomaly. But I'd say Atlanta first to the recovery, then DFW and then Orlando after that. uh living and breathing realistic? You're watching Netflix, you're reading books, you're scaling mountains. Well, so last year I had three things that I did. One was create fire primitively, two was build a shelter from scratch and sleep in and outside, and three was participate in the chess tournament. So I did that last year and this year it's build a lamp with my daughter from scratch. we already did that. It's I'm looking at my list. walk walk a hundred thousand steps in a day That's inspired from the book the long walk by Stephen King We'll see how that goes and then two other things carve chess pieces So learn how to carve and create chess pieces and then the last thing is play two songs on the guitar I do not know how to read music. I'm watching the videos for children on how to learn how to play the guitar and that's that's where I'm at now. Wow, do you document these like on-line or any videos or just your own? No, it's for me. I, yeah, I'll take a picture once once once it's done just to document that for for my own purposes but I don't I don't document it like the progression. Got it, wow. Okay, here, I thought you were gonna tell me your... binging law and order at 11 p.m. every night. seen it in a long time, but man, three Law and Order. That's top three favorite shows. uh Joe, first of thank you very much. I know I have a heartbreak over here. I sound very network corporate over here, but I know I have to go over here. But tell the audience how they can reach you, websites, email, phone number, whatever it is want to share, social medias. I'll make sure I put it the notes. I'm sure everybody here knows you. You're Googleable, as they say. just so the show notes have it. you can go to ashcroft capital calm Simple. Got it. No LinkedIn, no Instagram, everything is on there. on LinkedIn also, but I'm to the best of my knowledge I'm not on the other stuff at least I don't I don't do it, but I am on LinkedIn That's how we got connected so happy to connect with people on LinkedIn also Just so everybody at home knows, when I first started this podcast, I reached out to Joe and I asked him, hey, you're huge. You're famous online. I'm a guy who's thinking about doing a podcast. Why not get you? And most others similar uh in stature basically just ignored me. And he wrote me saying, I'd love to participate. uh know, schedule's tight. Come back to me after you did 30 episodes, give or take. And that motivated me. So when I was up to like episode six and I decided, hey, I think I'm done, I would find my old DM from Joe and say, hey, I just did episode six. I'm going to start bothering you in a few weeks. And same thing, 12, you know, 15, 23, 24, you know, whatever it was. And Joe, thank you very much. I appreciate you. coming on keeping me motivated. I'm not going to ask you to come in for my four year episodes. This is 38 or 39. But maybe 250th episode. I'll ask you to come back so I could pick your brain and be in awe. I really appreciate it Joe. Thank you very much. Another episode of The Wealth Clock with Steven Weinstock available everywhere. Subscribe, tell your friends, tag us, etc. etc. Reach out to Joe. tell him this was the best episode ever and he should share more pictures of his chess set. Thanks a lot. it,