March 20, 2022

JF2756: How One Cup of Coffee Kick-Started Her CRE Investing Career ft. Alessandra Thompson

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When a mentor offered to grab coffee with Alessandra Thompson if she was ever in town, Alessandra didn’t hesitate. The next day, she showed up to Nashville, and that coffee date ended with a business partnership. Alessandra shares how she made the bold move to move across the country from California to Tennessee, her experience as an underwriter and asset manager, and what she’s planning for the future.

Alessandra Thompson | Real Estate Background

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Ash Patel: Hello Best Ever listeners, welcome to The Best Real Estate Investing Advice Ever Show. I'm Ash Patel and I’m with today's guest, Alessandra Thompson. Alessandra is joining us from Nashville, Tennessee. She began her journey into real estate syndications after moving across the country. Alessandra now has two properties under management and she handles day-to-day asset management and operations. Alessandra, thank you for joining us and how are you today?

Alessandra Thompson: Thank you for having me. I'm doing really well. I'm happy to be here, excited to just be on the show.

Ash Patel: It's our pleasure. Alessandra, before we get started, can you give the Best Ever listeners a little bit more about your background and what you're focused on now?

Alessandra Thompson: Yeah. A little bit about me is that I'm originally from California. I started my real estate investing journey probably last March 2020. A little bit of education a couple of months before. I always knew that I wanted to just get into something that would free up my time and where I wanted to live, and also just help me out financially. This is something that I just wanted to really get educated in. I started out by just looking at all the different ways of how I could get out of my W-2. I wanted to get more passive income, so this is something that just clicked with me in the multifamily world.

I was just working in marketing in Los Angeles and it wasn't until COVID that I realized how unhappy I was with just going into an office, especially with the LA traffic. I was able to just get my life in order of where I wanted to be. I fell into multifamily, I found some mentors and people that were doing what I wanted to be doing, and I just got started and moved to Nashville to be in my market. I'm just super-excited to be here. I love the industry, I love the multifamily space. That's a little bit about me.

Ash Patel: I've got a lot of questions. First of all, you're in your mid-20s and you had this epiphany that you wanted more free time, you weren't happy with the W2. Do you know how many people I interview in their late 30s, 40s, and 50s that had just had that revelation? How did you come to this? I would Imagine a lot of people at that age are just like, "Alright, I'm going to work, I'm going to grind harder, and then I'll retire early. Or I'll save up enough money and then I'll move on to something else." How did you have this awesome mindset at that young age?

Alessandra Thompson: I think it's just that I've never been able to sit still in an office, and look outside and be like, "I want to travel the world and I want to be able to have the opportunity to spend more time with my family and friends." Also, my father passed away about four years ago and he was working until the day that he passed, and that just really struck a chord in me that that was something that I could not do. I wasn't able to spend enough time with him, I wasn't able to just be able to go on a trip with my family and friends, or go out somewhere, because it was always just about work. I think that life is meant for more than that. I think that there are just boundaries that need to be had, so I wanted to just be able to free up my time and be able to do the things that I want to do, when I want to do them. That's a lot of where it came from.

Ash Patel: Yeah, sorry to hear that, and thank you for sharing that. So you had that in the back of your mind... How did you bring yourself to take the action of leaving your job, pursuing real estate and moving to Nashville? Now, you said Nashville was my market - did you have the property first, or did you move to Nashville just because Nashville is awesome?

Alessandra Thompson: That's a really long story, but I'll get into the nitty-gritty. I was living in Los Angeles and then COVID happened. I didn't see anyone for three months, I was just like, "I'm just going to get my life together a little bit." My brother was living in Florida, he was doing door-to-door sales, and I just went. So I haven't seen anyone -- Florida seems like the other right place to go just to visit. So I went and visited, I stayed there for the entire summer, I started doing door-to-door sales with him. I made a good amount of money doing that while working my marketing job at the same time. I knew that I'd always wanted to get into real estate, so I was just like, "Okay, I'm going to put this money to use. I'm going to buy maybe a duplex and rent out one side."

It didn't seem like it was going to replace my job or my W2, and so I wanted to think outside the box of like, "How can I scale bigger?" That's when I started falling into multifamily. I got on Clubhouse when it first started. It was an interesting space, because I was just asking any question I wanted on the platform and just meeting different people, getting on phone calls, asking all the questions that I could, just jumping on the phone with people. My mentor now, the people that I work with were in the space and I just jumped on a call with her and she said, "That's awesome that you want to get in the industry. If you're ever in Nashville, let us know, we'll grab a cup of coffee." I was just jumping around from state to state, and I was like, "Okay, I'm going to go to Nashville tomorrow."

I packed my stuff up and I just moved to Nashville. I'd never been here before. I thought it was coming into old country, but it's actually very different than that. I showed up and I was like, "Hey, I'm here for coffee." I was still working my marketing job, so I had that security on the back end. So I just told myself to take that risk, take that action, see if there's any value that I can provide for these people. They happened to have an open position and they gave me the opportunity to start working with them, so I quit my W2 job and jumped straight into multifamily. I think through experience, I've been able to just grow a lot quicker and educate myself a lot faster by being like, that boots on the ground.

I took action, because if I didn't, then I would be in the exact same position that I was before. I think that in my mind, I was just like, "Well, the worst that can happen is that I move home, so I might as well just go test it out." I had really great time driving across the country, so that was a win for me. It has been working out, so I'm just really grateful and excited.

Ash Patel: I love your story. What did you end up buying first?

Alessandra Thompson: We went in on a property in Little Rock, Arkansas. It's a 36 unit and that was last July. There was a lot to be done; it was a 1935 build and we just went straight in, replaced property management. We ran into some issues and delays with closing, just because of the HUD statements. We also found there's a huge groundwater stream running under the property, and we had a big mold issue which just delayed closing a lot. I'm actually going there tomorrow, I'm going to drive there and take a look at it. I'll post it. So yeah, that was the first property that I closed on.

Ash Patel: Hold on, we're diving into some of this stuff. I'm very curious. When you say we, this is you and the person you had coffee with?

Alessandra Thompson: Yeah, we're partners.

Ash Patel: Okay. There's a story there that I need to hear. You had coffee and then you became partners. How did that happen?

Alessandra Thompson: I was able to come in and work with them as their underwriter and just doing day-to-day stuff, and now I've grown. Because I didn't know anything when I first started, so they didn't have to give me that opportunity. But they saw the hard work and determination, and so I was able to just start small, just doing basic things. Then I started to just keep educating myself, really looked through how the process worked, and now I'm working in asset management and going out to contractors, speaking with contractors, property managers, underwriting the deals still... I'm doing a lot of work on that end, and so I was able to just partner with them on the property.

We got it through our lender relationship. He actually lived in the area in Little Rock, Arkansas, so he thought it was a really good opportunity. It was on the MLS, it's a 36-unit. No one's going to go on the MLS to buy their house and be like, "I'm going to buy this 36-unit to be my residence." We were able to just go in there and get the financials. It's a great little deal, it's right off the main street of downtown, so that's just been so exciting to see. It had a lot of different challenges to it, so I was able to just grasp how to deal with them. I think that's the way that I've learned the most, is just through experience. So that started from coffee, yeah, to answer your question. [laughs]

Ash Patel: Were they blown away that they said, "If you're ever in town", and the next day, here you are?

Alessandra Thompson: Yeah. It's a funny story to always tell but I think it all just comes with taking that action and just showing up. Even if you don't know what to do, just take that next step because that's what's just going to propel you into the next step, and the next step. I wasn't very educated in it and so it just takes time, but they were blown away.

Ash Patel: I would be as well, that's incredible. I was going to ask you a question and you just answered it. The question was, what advice would you give somebody that's in their 20s, or even -- I don't think age matters. Somebody that's in a W2 job, hates it, realizes they're sacrificing all of their time, it's not where they want to be... And what you've just said, I think is the answer. Just take the next step; whatever step it is, take a step.

Alessandra Thompson: Take a step, even if that means reading a book about it. I think that just meeting people that are doing what you want to be doing, getting on the phone with people, going to meetups, having conversations, or attending certain webinars, it's all going to be helpful, because you're just going to build upon that, it's always going to take the next step. There's a lot of fear that's involved, and I think that's what people are afraid of is just getting out of their comfort zone.

I've been uncomfortable for the last year but I know that every time that I conquer the next step, I can look back and be like, "Well, I did this, so why can I do the next one?" I think it just comes with, "Okay, where am I going to direct my energy to, and what's going to get me to the next level?" It just all begins with believing in yourself, but also just taking that action and not letting fear guide you.

Ash Patel: I'm sorry, I'm blown away. You have an incredible outlook, a great mindset. Back to the Nashville deal - you also mentioned you found it on the MLS. Something I tell our Best Ever listeners often is to look for mis-marketed or mismanaged deals, and the MLS is a great spot to look, because a lot of people are looking to brokers. I have broker relationships, I look for off-market deals. While all of that is great, we're missing the low-hanging fruit, that new or inexperienced residential realtor that lists a multifamily or commercial property on the MLS; there's a ton of that out there. So I'm glad you brought that up as well. You ran into a lot of issues there... What was your role in resolving the mold issues, the HUD issues?

Alessandra Thompson: That was just speaking with our lender and speaking with the previous sellers of just how are we going to handle this mold issue. But it took a lot of just back and forth with the groups. My role I think came mostly with property management. I was just helping the transition of property management groups in the due diligence phases of how are we going to switch over the utilities, or collect the balances, and just working between those groups. We actually ran through the property management group that we hired secondly; they were not doing the job that they said they were doing, so we had to like pick up a lot of work, and so I was on the phone with contractors. I even posted Facebook Marketplace posts to get people into the unit. It was great, to just experience what day-to-day life looks like for a property manager. It's a lot of work, but it's just been helpful for me to learn. Really just a lot of communication and the due diligence of just switching over companies.

Break: [00:14:37] - [00:16:33]

Ash Patel: Alessandra, how much hand-holding have you received, or is this just learn as you go?

Alessandra Thompson: It's learn as I go. At first, I think the biggest challenge was speaking with contractors, like "What is the standard pricing? Where are we supposed to be? What's the timeline?" I think that I just had to get accustomed to that. It took a lot of asking a lot of questions and getting a lot of different quotes to compare. I think it's just been learn as I go. Jason Yarusi, the person that I work with has a great background in construction, so it's just in his brain. So I could just turn to him and be like, "What is this? What is that?" That's why I think it's so important to partner with people that are just doing what you want to be doing, that have that experience. I think that's the best strategy to just get into the place that you want to be, because you can just learn as you go from experts and people that are experienced.

Ash Patel: What's an example of a mistake that you've made and what would you have done differently?

Alessandra Thompson: Oh, man. I know I've made many mistakes, but I don't know why I can't think of one right now.

Ash Patel: Think of an embarrassing moment, an "Oh my God" moment, or "I can't believe I did this." Something that stood out, something crazy.

Alessandra Thompson: Oh, I can't even think of one, but I know that speaking of contractors I've probably said some dumb stuff, because I just wasn't accustomed to like, "How does this electrical thing work?" I'm sure I just sounded silly, but I genuinely cannot think of what I'm really...

Ash Patel: No, that's a good example. What would you have done differently? Because there's a learning curve, you talk to somebody who's been doing this for X number of years, and here you are asking a silly question. Is there something that you could have done differently?

Alessandra Thompson: Yeah. During the due diligence phase, there was one point where I was on the property and we were doing the inspection. I was on the property with 12 different contractors, and three of them getting different bids from everyone, so I started to just lose track of what I was supposed to be doing. I think that I could have been better at just writing everything down and recording what I was doing. Also, it's a space that I wasn't fully understanding yet at the time, so I think just being more educated and having someone that's more of an expert on-site would be helpful. Now I can go in there like a breeze and speak to those contractors.

Ash Patel: Like a boss.

Alessandra Thompson: Yeah. So I think it just takes practice. But I'm sure I've said some silly stuff.

Ash Patel: We all have. What was your next property?

Alessandra Thompson: We are doing a 20-unit motel conversion up in North Nashville, we're turning it into a short-term rental community, an Airbnb. This one has just been a full project. It's been really exciting, because I can just drive over there, it's like 10 minutes away, and just to really get down into the nitty-gritty of every layer of the process, versus the other property that is in Little Rock. It's just focusing on that communication with the property management that the business plan is going according to plan, which it wasn't with them at first, so that's why we had to also re-hire a new property management company; now it's going smoothly.

This one we're just handling on our own and it's just been getting people onsite, making sure that the schedule is just completely - no holes in it, because there are so many people in and out, like "Okay, the electrical needs to go here but we need to make sure this is done first; then the electrical needs to go back again." I think it's been really fun for me. I know it sounds stressful for a lot of people because we have to make sure we're doing a lot of everything on time, but it's fun for me to just see it happening before my eyes.

Ash Patel: How did you guys find this deal?

Alessandra Thompson: This one was actually through a broker.

Ash Patel: It was marketed as a hotel?

Alessandra Thompson: It was marketed as a motel. Yeah.

Ash Patel: Okay. The great idea of turning that into short-term rentals - doesn't Nashville have very strict rules on that?

Alessandra Thompson: They do. So with zoning, you'd want to just contact the zoning department. But here, because it was already set up as a motel, it was perfect because people are just coming in and out anyways. But there are a lot of issues with the zoning department.

Ash Patel: What's your role on this project?

Alessandra Thompson: I'm doing asset management, so I am always out there just with the contractors. It's a lot of work and just making sure everything's going according to plan, according to budget, speaking with the lenders on draws... Just out there.

Ash Patel: Asset Management sounds simple, but you're doing everything - the renovations, the lease-ups... You're going to run the asset once it's up and running as well, right?

Alessandra Thompson: Yeah, we have a third-party short-term rental property management group that's going to come in as soon as the property is ready. But because there's such an overhaul of work right now, it's probably not going to be online until April or May, just because there's so much to be done. It's been quite a journey. It's exciting because Nashville is such a good market for people coming in and out, especially - apparently, there's more bachelorette parties here than there are in Las Vegas.

Ash Patel: Nash Vegas.

Alessandra Thompson: Yeah. The numbers are great, and it's super exciting. I'm excited.

Ash Patel: How many hours a week do you work?

Alessandra Thompson: A lot. I feel like I couldn't tell you, because I wake up so early, like four in the morning. So I'll be emailing at four in the morning, or when I go home, and I'll be up on my email at 7pm underwriting a deal... It just doesn't end, but that's okay, because I enjoy it.

Ash Patel: The reason I asked that question is I want to contrast that to when you had your W2 job in that office, in traffic. Even though you may have worked less hours back then, the smile on your face now is amazing, because you love what you do and it's very fulfilling. Congratulations to you. Again, at a young age, having this stuff figured out... What are you doing to inspire other people?

Alessandra Thompson: I just want people -- especially there are not a lot of women in the industry, and I think that a lot of people just are afraid of getting into something like this because there's a lot to learn. But like we said, it just takes taking those small steps. I think to inspire other people, I love to set up Calendly links and just have phone calls. I like to help with mentoring others, so I'll just randomly get on a meeting with someone and overlook a deal with them that they're looking at. Help them point out what they're missing, how they could improve, who they can talk to, what they can just do to be stronger on their underwriting.

Then also just getting on panels or podcasts like this; I just want people to know that if they want help, I'm happy to just be a resource to them. I love helping others, and I want them to know that they are capable of doing something like this too, because I didn't use to think that I was, but I also just pushed that out of my mind. I was like, "Okay, well, why can't I do it?" Just letting other people know that it's possible to do what you want to do and make the leap.

Ash Patel: You are incredible and very inspirational, and I'm glad you're doing that. Where do you see yourself in five years?

Alessandra Thompson: As I said, I want to have that geographical freedom, so I would like to travel a lot, but I also would just like to keep scaling my portfolio with multifamily, possibly get into development at some point. I don't know what the future holds, but I think I'm on the right track to just leveling up each year, each year just trying to get better. Also just spending more time with family and friends. I love traveling, it's my main goal. I love eating at restaurants, so I'll be eating some more. [laughs]

Ash Patel: Do you get to travel right now?

Alessandra Thompson: Right now, a lot of US travel, so I've been doing some of that. Like Denver at the conference, that was fun. I'm going to go to New York for my friend's wedding, which will be good. But I haven't been out of the country since before COVID, so that's something that I really want to make sure I'm doing... But I've been very busy right now so I'll make it work, I'll figure it out.

Ash Patel: Good. What does your team look like right now? Is it just you in that one partner, or is it is a giant company?

Alessandra Thompson: There are three of us. It's Jason and Pili, they are amazing at what they do, and I'm so grateful to be a part of the team. So yeah we're just going to continue scaling and growing as a group, and seeing where we're going to go next.

Ash Patel: I am excited for you. Alessandra, what is your best real estate investing advice ever?

Alessandra Thompson: Just get started. I think that just take action, don't let fear guide you. I think success lies on the other side of fear. Just know that you're capable of doing anything that you set your mind to. Just take action.

Ash Patel: Alessandra, are you ready for the Best Ever lightning round?

Alessandra Thompson: Oh my gosh, these stress me out, but yeah.

Ash Patel: Well, you're stressing me out now. All right, listen, let's take a breath, and let's get through this. Alessandra, what is the Best Ever book you recently read?

Alessandra Thompson: Oh man. I read the Psycho-Cybernetics book is really good. Just shifting your mindset of the way that you see yourself. I think that once you shift the way that you see yourself, then you can shift the way that you act on daily actions. That's a great book, everyone should read it.

Ash Patel: Alessandra, what's the Best Ever way you like to give back?

Alessandra Thompson: Give back? For friends and family, I love cooking a home-cooked meal and sitting down at the table, just being there together and checking in on everyone. That's why I love to get back to my family and friends.

Ash Patel: Alessandra, how can the Best Ever listeners reach out to you?

Alessandra Thompson: They can reach out to me at They can find me on LinkedIn, Alessandra Thompson. Send me an email, that would be great.

Ash Patel: Your information will be in our show notes as well. Alessandra, it was actually a very good pleasure meeting you at the Best Ever conference. Glad we got to do this podcast together. Thank you for sharing an inspirational story. Moving from California to Nashville, showing up because somebody invited you for coffee, showing up the very next day. You're on your way to building a great portfolio. Thank you for sharing that inspiration with us and the Best Ever listeners.

Alessandra Thompson: Thank you so much for having me. I'm looking forward to hearing the episode. It was so great to meet you at the conference.

Ash Patel: Thank you again. Best Ever listeners, thank you for joining us. If you enjoyed this episode as much as I did, please leave us a five-star review and share the podcast with anyone you think can benefit from it. Follow, subscribe, and have a Best Ever day.

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