8 Real Estate Deals in 2 Years While Working Full-Time (Raising 4 Kids)

23 Mar 2026 · 47 min · 21 chapters

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In short

Molly Shepard shares how she and her husband built a fast real estate portfolio while working full-time and raising four kids (including a foster daughter), including their first flip, deal sourcing, funding, rehab decision-making, and lessons learned (including a $9,000 termite/hidden-damage loss). She also discusses mindset shifts for rookies and operational changes like using AI and standardized inspection forms.

Guest backgrounds

Molly is an Army veteran and a full-time training loan officer at the nation’s largest VA lender. Her husband Kyle previously flipped their primary residences and later became a full-time investor. They have four kids and foster a daughter; they focus on St. Louis County and St. Charles County.

Key claims

Rentals aren’t passive; investing requires active systems. They listened to Real Estate Rookie for ~2 years before acting. They made 8 flips in 22 months, closed eight flips, bought two rentals, and used hard money with minimal cash outlay (interest/points later). They always make offers below asking price.

Notable examples

First “granny house” deal: bought for $115k, rehab ~$35k, sold ~$200k (listed $195k). Loss on a later flip: no inspections; missed missing gutters and ~$9k termite damage. They use AI to review property videos and estimate issues/parts, and they market to sellers via social media and assisted living/memory care partnerships.

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

Tap a time to open that second in VO

Molly's Journey into Real Estate

3:10 to 5:00

Hear about Molly's journey balancing a full-time job and a family while flipping houses.

“So what made you decide to tackle all of this going on in your life at the same time of doing your first flip.”

Breaking the Cycle of Time Constraints

5:00 to 6:40

Molly shares how she overcame time constraints to pursue real estate investing.

“Did you make any changes in your life or sacrifices during that time period when you were kind of learning, researching, and growing and ready to do the first deal?”

Finding the Right Mindset for Investing

6:40 to 8:00

Molly discusses the mindset shifts necessary to embrace real estate investing.

“returns, and start investing in just minutes.”

Getting Support from Family in Real Estate

8:00 to 9:30

Molly talks about how she convinced her husband and family to support her investing dreams.

“The portfolio features 4 ,700 single-family rental homes spread across the booming sunbelt.”

Building Confidence in Real Estate Decisions

9:30 to 11:30

Molly explains how she and her husband developed confidence in their real estate ventures.

“Don't just dream about real estate, make it happen with PropStream.”

Leveraging Industry Connections for Success

11:30 to 14:01

Molly shares how her work relationships helped her navigate real estate investing.

“And then I feel like literally after listening to episode after episode, it was finally like somebody shook me and said, just do the thing.”

From Numbers to Relationships in Real Estate

14:01 to 16:20

Learn how building relationships with contractors and investors can enhance your real estate business.

“He's not quiet necessarily, but more not outgoing, not as outgoing as I am.”

The First Deal: A Granny House Journey

16:20 to 24:10

Discover the story behind the first property flip and the challenges faced during the process.

“We are here with Molly and let's go back to the beginning of your very first rookie deal.”

Overcoming Obstacles in Real Estate Deals

24:10 to 28:00

Understand how to address challenges and provide solutions for motivated sellers.

“I mean, the seller has been messaging me and expresses to me how this has been such a burden on her and things like that.”

Funding the First Real Estate Deal

28:00 to 29:20

Learn how hard money financing helped fund an initial real estate investment.

“item that just says, we buy houses and here's what we can provide to you in order to make your life easier.”
Show all 21 chapters

Mentorship in Real Estate Investing

29:20 to 31:10

Discover the importance of mentorship and relationships in successful investments.

“monthly interest payments, which the concept was wild to me.”

Family Connection in Property Sales

31:10 to 33:55

Hear about a touching real estate deal that kept a family legacy alive.

“And I think, I think that is huge to their success.”

Lessons Learned from Flipping Mistakes

33:55 to 36:10

Understand the critical lessons from losing money on a property flip.

“Yeah, it was it was really, really cool.”

Improving Property Evaluation with AI

36:10 to 38:30

Explore how AI technology is changing property evaluation processes.

“So my husband views every single property.”

High Volume Deal Flow Strategies

38:50 to 40:50

Learn strategies on increasing deal flow and making offers in real estate.

“Molly, you said something pretty incredible off camera, but that in the last 90 days, Kyle, your husband, has walked 114 properties, made offers on 47 and bought five.”

The Role of Realtors in Property Acquisition

40:50 to 42:00

Discover how partnerships with realtors can enhance property acquisition efforts.

“I'll never forget when he came home from one of these properties.”

Building Investor Relationships Through Open Houses

42:00 to 43:19

Learn how Molly and Kyle leverage open houses to connect with new investors.

“market about 10 to 12 every Friday and new investors, a lot of them, we have a name for ourselves now.”

The Importance of Making Offers

43:20 to 44:48

Discover why making offers is crucial for new investors, regardless of the asking price.

“with investors, whether they buy one of the houses or not.”

Overcoming the Fear of Insulting Sellers

44:49 to 47:20

Find out how to handle the fear of making low offers and maintaining relationships with sellers.

“how many of your deals are actually below what the original asking price was?”

Long-term Opportunities in Real Estate Negotiations

47:21 to 49:58

Learn about the potential for future deals even after initial rejections.

“I think I might've talked about this in a podcast a while ago, but when I first started trying to invest, again, I was focused on Shreveport, Louisiana.”

Connecting with Molly and Podcast Wrap-up

49:59 to 50:30

Get details on how to connect with Molly and a recap of the episode.

“Well, Molly, thank you so much for joining us today.”
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Transcript

Automatic transcript. May contain errors.

0:00We all joke that rentals are passive, but if you're spending nights matching receipts or guessing what a property earned last month, that's not passive at all.

0:07Tony Robinson:Baselain fixes that part of landlording, the financial chaos. Their banking and AI bookkeeping system automatically tags every transaction, updates cash flow insights in real time, and builds the reports you need for tax season. You can even automate transfers and move money around without paying wire fees. It's just cleaner. Sign up at baselain.com slash BP and get a$100 bonus. Baselain is a financial technology company and not a bank. Banking services provided by ThreadBank. Member FDIC. For decades, real estate has been a cornerstone of the world's largest portfolios. But it's also historically been sort of complex, time-consuming, and expensive.

0:38Tony Robinson:But imagine if real estate investing was suddenly easy. All the benefits of owning real, tangible assets without the complexity and expense. That's the power of the Fundrise flagship fund. Now you can invest in a$1.1 billion portfolio of real estate, starting with as little as$10. The portfolio features 4 ,700 single-family rental homes spread across the booming sunbelt. They also have 3.3 million square feet of highly sought-after industrial facilities, thanks to the e-commerce wave. The flagship fund is one of the largest of its kind. It's well-diversified, and it's managed by a team of professionals.

1:13Tony Robinson:And it's now available to you. Visit Fundrise.com slash bpmarket to explore the fund's full portfolio, check out historical returns, and start investing in just minutes. Carefully consider the investment objectives, risks, charges and expenses of the Fundrise flagship fund before investing. This and other information can be found in the fund's prospectus at Fundrise.com slash flagship. This is a paid advertisement. Do you ever notice how every passive investment somehow turns into a very active lifestyle? Active spreadsheets, active phone calls, active stress. Here's a better question. What if you could buy brand new construction homes, 10 % below market value, in the best markets across the country without making real estate your second job?

1:49Tony Robinson:That's exactly what Rent to Retirement does. They're a full-service, turnkey investment company handling everything for you. In some cases, investors get 50 % to 75 % of their down payment back at closing, plus interest rates as low as 3.75%. They've partnered with BiggerPockets for over a decade, helping thousands invest smarter. If you want to do the same, visit biggerpockets.com slash retirement to learn more.

2:13Ashley Kehr:Most people here are me, veteran, four kids, foster mom, and full-time W-2 and assume there's no room left in the day for anything else. Molly Shepard heard that and thought, perfect time to flip a house.

2:24Tony Robinson:In just 22 months, Molly and her husband Kyle closed eight flips, picked up two rental properties, and have more in the pipeline all, while Kyle made the leap to full-time investor, and Molly kept her W-2 at the nation's largest VA lender. And today, she's here to show you how exactly they made that.

2:46Ashley Kehr:This is the Real Estate Rookie Podcast. I'm Ashley Kerr.

2:49Tony Robinson:And I'm Tony J. Robinson. And with that, let's give a big word and welcome to Molly. Molly, thank you for joining us on the Real Estate Rookie Podcast today. Excited to have you.

2:56Ashley Kehr:Thanks for having me. I'm excited to be here. Molly, before we get into the deals, I want to paint a picture for our listeners. So, as we mentioned in the intro, you're an Army vet, you work full-time training loan officers, and you have four kids, including a foster daughter. So what made you decide to tackle all of this going on in your life at the same time of doing your first flip. Where does real estate fit into your life at this time? I think I have always kind of gone against the grain a little bit. So that kind of came naturally. But when I started working in real estate on the loan side of things, I really started becoming interested in the flipping and investing side of things.

3:42That's kind of what got me started. Um, so yeah.

3:49Tony Robinson:But I think what a lot of rookies hear, Molly, in your story is that you've got a lot going on and that mimics a lot of what they're feeling as well. And there's this really weird paradox over here often where people want to invest in real estate so that eventually they have more time in their lives. They have more time to maybe be job optional or they can go part-time or they can just have more time to do whatever it is they want to do. But yet they can't invest in real estate because they don't have time. And it becomes this like securitist thing where it's like, well, you can't break the cycle if you never do the thing that's going to give you the time.

4:20Tony Robinson:Right. How did you not fall victim to that same mindset or getting stuck in that same loop? I mean, I think I have that same mindset of like, I do want the option to be W-2 optional. I do want the ability to travel, you know, across the world, not just like in the States with our family. And I want to be able to do that when we're young and like not wait to travel until we're, you know, retired at 70. So I think working really hard now is going to pay off in the long run, even if it seems like a lot now.

4:54Ashley Kehr:And Molly, was there anything that you were doing that maybe someone else isn't doing that's giving you that step ahead as far as taking on that first flip? Did you make any changes in your life or sacrifices during that time period when you were kind of learning, researching, and growing and ready to do the first deal? I think a lot of times I hear people say, I don't have the time or like, I don't know how you make the time. and everyone has the same 24 hours. And I think it really comes down to what do you do at that time? So, you know, for instance, in the mornings when I walk, like I listened to rookie real estate for almost two years before we pulled the trigger.

5:34And then when I am at my kid's soccer practice, I am on the phone with investors or I am working numbers on deals. Yes, I'm still paying attention. I'm still watching them. But like, I just kind of make sacrifices there so that I still am able to be present, but also like be efficient with my time.

5:53Tony Robinson:For decades, real estate has been a cornerstone of the world's largest portfolios, but it's also historically been sort of complex, time consuming and expensive. But imagine if real estate investing was suddenly easy. All the benefits of owning real, tangible assets without the complexity and expense. That's the power of the Fundrise flagship fund. Now you can invest in a$1.1 billion portfolio of real estate, starting with as little as 10 bucks. The portfolio features 4 ,700 single-family rental homes spread across the booming sunbelt. They also have 3.3 million square feet of highly sought-after industrial facilities, thanks to the e-commerce wave.

6:30Tony Robinson:The flagship fund is one of the largest of its kind. It's well-diversified, and it's managed by a team of professionals. And it's now available to you. Visit fundrise.com slash bpmarket to explore the fund's full portfolio, check out historical returns, and start investing in just minutes. Carefully consider the investment objectives, risks, charges, and expenses of the Fundrise flagship fund before investing. This and other information can be found in the fund's prospectus at Fundrise.com slash flagship. This is a paid advertisement. People love to call real estate passive income, which is interesting because most of the investors I know are very busy.

7:02Tony Robinson:Busy finding deals, busy managing teams, busy worrying they picked the wrong market. Rent to retirement flips that model. They help investors buy turnkey new construction homes, often 10 % below market value in top rental markets across the country. Their local teams handle the build, the property management, and the details so you don't have to. In some cases, investors even receive 50 to 75 % of their down payment back at closing, and their interest rates as low as 3.75%. They've been trusted partners with BiggerPockets for over a decade. And if you want to learn more, visit biggerpockets.com slash retirement.

7:36Tony Robinson:For decades, real estate has been a cornerstone of the world's largest portfolios. But it's also historically been sort of complex, time-consuming, and expensive. But imagine if real estate investing was suddenly easy. All the benefits of owning real, tangible assets without the complexity and expense. That's the power of the Fundrise flagship fund. Now you can invest in a$1.1 billion portfolio of real estate, starting with as little as$10. The portfolio features 4 ,700 single-family rental homes spread across the booming sunbelt. They also have 3.3 million square feet of highly sought-after industrial facilities, thanks to the e-commerce wave.

8:13Tony Robinson:The flagship fund is one of the largest of its kind. It's well diversified, and it's managed by a team of professionals. And it's now available to you. Visit fundrise.com slash bpmarket to explore the fund's full portfolio, check out historical returns, and start investing in just minutes. Carefully consider the investment objectives, risks, charges, and expenses of the Fundrise flagship fund before investing. This and other information can be found in the fund's prospectus at fundrise.com slash flagship. This is a paid advertisement.

8:37Ashley Kehr:Thinking about wholesaling or flipping your first property, but not sure where to start? The truth is, deals don't just fall into your lap anymore. You need to go out and create opportunities. That's where PropStream comes in. With PropStream, you get instant access to over 160 million properties nationwide. Use 20 pre-built lead lists such as pre-foreclosures, tax delinquencies, and vacant homes to find motivated sellers fast. And now, PropStream has integrated batch leads and batch dialer to provide you with a complete all-in-one solution. That means you can not only find motivated sellers, but you can also reach out right away.

9:10Ashley Kehr:Skip trace phone numbers free on select plans, then send postcards, emails, or call sellers directly. Don't worry if you're new. PropStream also gives you AI-powered insights and comps that are over 99 % accurate, so you know you're making smart offers. Plus, you'll have access to PropStream Academy to guide you step-by-step. Start your 7-day free trial and get 50 free leads at propstream.com. That's P-R-O-P-S-T-R-E-A-M.com. slash BP. Don't just dream about real estate, make it happen with PropStream. You know that purple ShopPay button at checkout? The one that lets you tap and buy instantly?

9:45Ashley Kehr:That's Shopify. Shopify powers millions of businesses and 10 % of all e-commerce in the U.S. You can build a store fast, reach customers with email and social campaigns, and manage everything in one place. And ShopPay helps boost conversions with one of the best checkouts on the planet. See less carts, go abandoned, and more sales go with Shopify and their ShopPay button. Sign up for your$1 per month trial today at shopify.com slash rookie. Go to shopify.com slash rookie. That's shopify.com slash rookie.

10:14Tony Robinson:How do you think your experience in the military maybe shaped your ability to maybe have a little bit more discipline than the average person, if at all? Yeah. Flexibility, I think. You know, everything, especially in real estate, everything changes daily, hourly, by the minute. And that was really easy for me to do coming into real estate because I was so used to doing that in the military already. And I think that comes down to a lot of places in my life. You know, being a foster parent as well, it's just like things change all the time. And we just have to adjust and adapt and overcome is what I like to say all the time.

10:51Tony Robinson:Now, you talked about binge watching, you know, the Rookie podcast and doing that, doing your 5 a.m. walks. But for a lot of folks, they get stuck in that analysis paralysis phase. Because I think you mentioned it was like two years. What finally broke you out of that just consumption phase to push you toward actually taking action? After listening to so many and them all, I feel like having the similar bottom line of like, just go do the thing, pull the trigger and figure it out. I think the fear of knowing that you're going to make mistakes. But as long as you kind of cross your T's and dot your I's on the basics and like know that the numbers work, the rest will fall suit.

11:32I think that was really helpful to me. And then I feel like literally after listening to episode after episode, it was finally like somebody shook me and said, just do the thing.

11:42Ashley Kehr:Now, during this time, was your husband on board from the first day you listened to Real Estate Rookie? and also your family and people around you, were they on board with you doing this? No. So my husband had flipped our two previous primary residences while we were living in them. And it was nothing crazy, just more cosmetic. And I knew that he just wasn't satisfied with his job. I could just tell he worked behind a computer all the time and it just wasn't his thing. And I was like, why don't you do this full time? And he was like, are you out of your mind? Like we have four young children, like elementary school and under.

12:22So he was not on board at first. And then I was like, what's the worst that can happen? You go get another job like that. That's really the worst that could happen. Right. So when we went to our parents and said, hey, Kyle's going to quit his job and we have four young kids. They thought we were out of our minds, which is common. Right. Right. Becoming foster parents and being in the military, my parents already know that, like, what are we going to hear from her next? But they were very leery at first. And I kind of told them the same thing. Like, what's the worst that happens as we go? He goes and gets a W-2 job if it doesn't work.

13:01So that's kind of the mindset that we've had. And literally, it has been life changing positively since then.

13:09Tony Robinson:And so Molly, let me ask, because a lot of people that are listening are much like you, where they were, they were in this kind of solo mode of consumption and, you know, obtaining all of the knowledge and getting that, that exposure to real estate investing. How did you actually get Kyle to the point where he believed in it as well? Like, what did those conversations look like? How did you get him on board with the idea of investing in real estate before actually even getting him to go full time? Yeah, I just kept reminding him, like, do you want to live your life doing the same thing just because it's easy and habit, right?

13:43He's kind of a creature of habit. And he would, you know, side eye and I mean, but it's, you know, it's just easy and normal. And I was like, but I don't want to live that life forever. So why not just step outside the box? It's so funny. He's not quiet necessarily, but more not outgoing, not as outgoing as I am. And when we would go to look at these houses at first, he was just quiet. He's like, you know, I'll just work on the numbers side of things. Now he's the one that is calling the contractors, communicating with the inspectors and like building these relationships and also reaching out to new investors and like getting them to pull the trigger of like, hey, if I did this and I was such a creature of habit, I think you can also do the same.

14:35Ashley Kehr:Now, on your side of things, you've worked for the VA and helping other people purchase with lending options. How has that benefited you having those relationships and working with those investors on your side of things? Yes. So first, I don't work for the VA. So I work for the top VA lender, purchase lender. Can you ask that question again? Sorry. Okay. So with your job now, your W-2 job, you work with the largest VA lender. So you're seeing people go in for purchase properties. You're helping them through the lending process. You kind of described your husband's responsibility and things. Have you used your W-2 and the things that you have learned from it and your skill set to kind of help you guys in your business of doing these flips and getting these rental properties?

15:27Absolutely. I think one of the main reasons why I became interested is because I know the background of a lot of the brothers and sisters that I served with. A lot of them are not only first-time homebuyers, they're first-generation homebuyers. And they're not coming in and buying$500 ,000 houses off the bat. And I wanted to find a way to, in my own community, create some flip properties that are affordable and able for these people to actually live in because I see the finances and the stress that that much must have on them. And so that has had a huge impact on also who we rent to is we focus on homeless veterans and veterans that need housing of any sort.

16:18Ashley Kehr:Okay, coming up, we're going to take a short break, but Molly's going to walk us through the deal that started it all, a 50-year-old granny house full of 50 years of junk and the specific mistake that cost them$9 ,000 on another deal that every new flipper needs to hear. We'll be right back after this break. Okay, so welcome back. We are here with Molly and let's go back to the beginning of your very first rookie deal. So a neighbor of a former business partner actually passed away and you got the opportunity to see this house and it ended up being a true granny house. So take us inside that property and what did this deal look like?

16:59Yes. So it was wallpaper, old flooring, yellow tile, your typical, they have lived in there forever and not updated a bit of it. It was very clean, just a lot of junk. So you had to be able to see past all the junk to kind of see what you could do with it. But when we got in there, my husband was really excited to do all of the things. And when we came in, you know, when we had our mentor come in and we were like, these are the things we want to do. They had to really set the market straight of like, hey, you're not flipping this for yourself. You're flipping it for the area. And I know that you want to do all of these extreme updates, but I don't necessarily know that that's what you should do in that area, which was really, really helpful for us to get in a different mindset when going into the split.

17:56Tony Robinson:Can you talk about that? How do you determine how much is too much rehab? Because I think that is a mistake that a lot of newer investors tend to make is that they think about renovating a place for themselves to live and not necessarily who the end buyer is. How do you walk that line of not doing so little that it doesn't actually get the sales price you're hoping for, but not doing so much that the deal actually becomes unprofitable? Yeah, I think it was huge to realize, hey, comparables in the area had three ones, right? Like they were three bed, one bath. So like adding a bathroom in the bed or in the basement, like, was that going to benefit us as much as we thought it was?

18:35And it's going to take more time. It's going to take different permits when it's like, okay, if we could just go in and do flooring and cabinets and paint, we're going to be able to flip it much quicker. And it's going to still meet the needs of our buyers in that area. So definitely looking at comparables, recently sold properties and seeing what they've done is extremely helpful in all of the markets that we've touched.

19:03Ashley Kehr:Now, Molly, can you share with us the numbers on this deal? What was the asking price? What did you purchase it for? What was the rehab, the timeframe, and what did you up selling it for? So this property we purchased for$115 ,000 and then we put about$35 ,000 in rehab into it and we sold it for, we listed it for$195 ,000 and we sold it for$200 ,000.

19:27Tony Robinson:Wow. That's a great first deal. Yeah. Is that purchase price typical of that area? Yes. And for the listeners who don't know, where are you based out of? I'm in St. Louis. So we focus on St. Louis County and then St. Charles County are our two areas. So I guess a few questions here, right? I want to talk a little bit about actually finding the deal. Because obviously you have to find a great deal to be able to get that kind of margin, right? You bought it at 115, you said 30 grand in, all in for 145. You sell for almost 200. So, you know, good margins there. But how did you actually find the deal?

19:58Tony Robinson:I know that we mentioned that it was like a friend of a friend. But what did that actually look like in practice? Yeah, so our previous business partner, she had reached out because her mom actually lived in the house across the street from this lady. And the family kind of reached out and was like, hey, I know that your daughter is getting involved in this. Would you guys want to do it? And they were so grateful. It was really cool. Our previous partner, she took them to do a final walkthrough and there were lots of tears had. And it was really cool to see that they knew that we took really great care of the property because I think that's an area that's missed a lot is like, oh, they'll just sell it to some flipper and they never see or hear from it again.

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20:44And that's an area that we've used, kind of a tactic that we've used moving forward. We focus on letting them know, hey, we will share with you as much as you want to know, you know, progress photos and final photos, all of those things. We would love to share those with you if you want that. And especially to give you kind of, especially if the property has been in your family forever, we want to be able to give you that peace of mind and, you know, burden, like, left off of you after selling the property.

21:20Tony Robinson:But how did that seller know, Molly, that you and that first partner were even options? Like, how did the word of mouth actually get around to that person? That's what I'm most curious about. Yes, social media. Yeah. I thought it was crazy. I think that was a really big thing in the Rookie podcast when I would listen. And I was like, how are you saying that we buy houses, right? You're like, we buy houses. And I'm like, that is not my money. I'm not buying anything. So that was really hard for me to get over of, hey, I can say this. And they don't need to know the background as long as the property is being taken care of.

22:00Right. So, uh, the, we buy houses thing, we were posting a lot on social media and it did feel very, um, what's the word? Like I felt very out of place. Like imposter syndrome in a sense. Yes. Imposter syndrome. Like totally because I'm like, I'm not buying the house. Like, what, what am I talking about? Um, but I'm can, I'm controlling all of those factors that they don't have the capacity to carry themselves. So like, I'm actually taking a burden off of somebody else.

22:31Tony Robinson:But Molly, what, like, what were you saying? And where were you posting? Like, obviously it struck a chord. So what was that? Yeah. Our stories were very like our Facebook stories, Instagram stories. At that point, we didn't have TikTok. Now we're very involved with the TikTok videos, but we were just sharing and saying we buy houses. Like if you have an ugly house or a divorce house or anything, probate houses, anything that is a burden to you, like reach out to us and we'll make it happen. And I think that was also another part of pulling the trigger initially really had to do with feeling comfortable, not knowing the answers to everything, but knowing where to find the answers, right?

23:13Like I knew if somebody came to me with a probate deal, I'm like, I don't know what I'm doing fully. But knowing that I have the resources and community to find the answer to that. And that's not something that the seller is, they can't figure out right now. So I'm helping solve that problem for them.

23:32Ashley Kehr:I've bought probably four properties that were either from an estate or like there was like one right now that I'm literally just closing today is that the owner of the property is in assisted living and the family is in a trust and his children are actually the trustees and have the decision making or whatever and dealing with them. And I cannot tell you how much of a burden this property has been for those children that are selling it for him. Just having to go to the property to meet the inspector, the appraiser, all of these different things, and then getting the house cleaned out. I mean, the seller has been messaging me and expresses to me how this has been such a burden on her and things like that.

24:25Ashley Kehr:So there are those motivated sellers out there who just want to get the property sold because it's not worth the headache, the hassle of like putting it on the market, going through, you know, different offers. And then, you know, maybe that offer falls through and then it's going back on the market and things like that. So there are definitely people out there that are just motivated to be done with it. And like one of the people that I had purchased from that was an estate, like they were just so sad about their mom passing that they just wanted to be able to move on with their life. And they just couldn't feel like they could like finish grieving until this part was also done of getting the house sold, getting their things cleaned out and everything like that?

25:05Ashley Kehr:We've actually focused on that. So we recently kind of going into the new year with our new goals, I was like, I really have a passion for, I am a pretty empathetic person and I love helping solve someone else's problem for them. Right. So we have actually recently started going to assisted livings and memory care facilities and meeting with their directors and saying like, hey, we will come in and help your new clients of somebody that's already dealing with the stress of having to put a family member into care. Like, hey, let us take the burden off instead of them going to find some random person that they're not sure their property is going to be taken care of.

25:51Let us take that on for them and then provide whatever services they need for us. If they want us to clean out the junk, if they want to clean out the junk themselves, if they want update pictures, all of those things, just adding another layer that I think it could be a really cool niche, hopefully coming into this new year.

26:12Ashley Kehr:Yeah, that is such a great idea. What a great relationship to build. How have those conversations gone? Have they been receptive or how has that worked out? We had to figure out first when you like go into those, like into the assisted living places, you commonly are talking to the, you know, front desk person. And we figured out like, hey, we actually need to call these places ahead of time and meet directly with the director. And that has been so much better. And we've seen a lot more, you know, success. They've like, a lot of them have been like, we have never had someone come in to kind of, you know, offer this service.

26:51And it's not something that like, you know, we want to, you know, there isn't any referral compensation between us and the assisted living. It's just saying, hey, if you're going in with a packet of stuff to give these people that are in such a, you know, distraught state of mind, let us be like a way to calm their mind a little bit and take care of that property and be able to close as quick as, you know, a lot of people, I feel like in that same boat, you might have already like have dealt with this, but they think that they can rehab it or they think that they have the funds. And then, you know, two months down the road after paying that mortgage payment and realizing like, I don't have seven grand to drop on an HVAC system, then you become an option when maybe originally you weren't an option.

27:40So I think still getting your name out there and letting them know the services you provide can be extremely beneficial.

27:47Ashley Kehr:So are you giving them pamphlets, business cards, brochures that they can hand out? Okay, cool. Just kind of like a five by seven, just kind of a postcard-like item that just says, we buy houses and here's what we can provide to you in order to make your life easier. Which are very inexpensive to create online and get printed. Yeah. What a great idea.

28:12Tony Robinson:That's a great guerrilla style type marketing, Molly. I love that approach. But you mentioned someone not having the funds, 7K to pay for an HVAC system. How did you actually fund this first deal? Was it just money you had saved up? Was it private money, hard money? Walk us through how you actually put together the 115 for the purchase plus the 30K for the renovations. Yes. So this one was hard money. We had saved up some funds when my husband, well, he was still employed at that time during the first deal. And then when he, when we were doing, when he was flipping the property and also employed, we were like, yeah, this isn't going to work.

28:51And that's kind of when he dipped. So we originally bought the property in February of 2024 and he quit his job in May of 2024. But yeah, this one was hard money.

29:03Tony Robinson:Got it. And hard money covered what percentage of your total cost and what did you use to fund that difference? Yeah. So they actually covered everything up front. So yeah, we just came in and paid the interest on the back end and our points on the back end. And we came out of this deal, we put in$0 of this deal besides our monthly interest payments, which the concept was wild to me. Yeah. So this is in 2024. So my very first real estate deal was a very similar kind of setup where I had zero cash out of pocket. I just have to pay the monthly interest costs. But I found that it's been a little less common kind of post, especially post COVID.

29:46Tony Robinson:Who is this lender? How did you find them? Yeah. So we found them from the real estate community in St. Louis. We they are big with helping first time flippers with their projects. So they actually were the ones that came in when Kyle had all of these big ideas and they were like, not necessary. So they were such a great mentor to us. And we send a lot of people their way when they are thinking about using hard money. That's incredible. I know most hard money lenders are the opposite. They want you to have some experience.

30:28Ashley Kehr:But if you think about it, you give somebody a chance and they end up becoming an investor, you've built that relationship for a long period of time where most lenders are waiting until you've already got deals, then starting to build that relationship where they're getting in the forefront and trying to get your business and building that strong. And I feel like it's one, a drill sergeant in basic training always told me like, we'd rather someone come in that has never shot a gun before than someone who is, you know, a pro hunter because we can teach them the ropes. And I think that's kind of the tactic that they take is like, hey, we can teach you all the things the way we want you to learn it.

31:10Right. And I think, I think that is huge to their success.

31:14Ashley Kehr:Yeah. That's so funny. Like employers will even say that sometimes like in different industries, like we'd rather someone brand new that has bad habits from the other job they were doing. But Molly, I think it just goes to show that there are so many different ways to fund

31:30Tony Robinson:your first deal. And as long as you find a deal that's good enough, if you can get it in front of the right people and enough people, sometimes you can find someone that's going to fund everything for you, right? And you just got to kind of worry about the carrying costs. So the first deal sounds like a home run deal, right? You do everything the right way. You find a great deal. You get great lending. But you actually said that your fourth property is one that you're most proud of. And I know it involves a woman who lived there for a long time, who maybe who wasn't in the best position. Walk us through that fourth deal and why you feel that one is one that really stands out to you.

32:03That connecting piece, right? So we found this deal. Our kiddo's in-home daycare provider, it was her sister who we bought the property from. And she had lived there for a long time. And we came in and flipped it. And then on the back end, it's like so cool. to even think about. We didn't know this. The agent came in and was like, hey, we have a buyer and all of these things. And after going under contract, we found out that the buyer was the lady who owned the home's daughter. And she was going to now have this property as her first home. And now her grand, the lady's grandkids are now going to like be living in this home.

32:57And I just, it's so cool to think about and the different, you know, she had lived there for so long and then to be able to walk into the same property and have such a different eye for it. And now your kiddos and grandkiddos are living in it. Just really cool, full circle moment for us.

33:15Ashley Kehr:That really is such a cool thing to find out that you were able to provide that service for someone and their family and to keep the property in the family. Because sometimes I think there is like this like bad reputation of investors of like, oh, you're stealing from grannies, you know, you're taking their home, you're cutting yourself a deal and they're getting the shaft and stuff. But the fact that the same family actually went and came and bought the house at the price you were asking for. And, you know, it shows that they didn't actually end up with a bad deal. They they thought it was a good deal in the end.

33:55Yeah, it was it was really, really cool. I think about that property all the time because I'm like, gosh, how cool it must be for her to like pull up in the driveway of like now her kid's house that she lived in and like know the memories that are being created. and that those same kiddos grew up in that house. Really cool.

34:12Ashley Kehr:So Molly, you've done eight flips in 22 months and that's pretty fast. Now you told us the deals that you've made money on, but have you lost any money on some of the deals and what were maybe some of those lessons that you learned along the way? Yeah, so we did lose money on one of our flips. We did not do our due diligence when going to look at the property, right? Sometimes you trust other eyes on the property and don't look at it fully or you're like, oh, okay. I think when we started doing multiple at a time, it gets easy to forget the really important things. So we went into this property.

34:54We did not get any inspections on it, which sometimes is common for flip properties. But this one was a little bit different. We didn't notice that it didn't have gutters on it. So the rain, all the water was just dropping directly back into the foundation. And then come to find out there was$9 ,000 worth of termite damage that we did not see. And, you know, I'm surprised nobody fell through the flooring. The lady had lived there for a very long time. And that was a wholesale deal, which we have not done too many wholesale deals. And it was really just letting our checks and balances slide because we were working so many properties.

35:46And I think it really it was such a good learning lesson for us to come back and be like, hey, there is no reason why this should have happened. but we let it slide because, you know, there were a lot of other things going on in the pipeline. And it has really kept our checks and balances moving forward to not make mistakes like that.

36:08Tony Robinson:So what's changed now in your process to try and avoid repeating that same mistake? Yeah. So my husband views every single property. We take video of every property. AI has change the flip game when it comes to being able to view a property quickly and efficiently. And if we miss something, AI is going to catch it.

36:30Ashley Kehr:Let me ask you about that because my mind is just like, oh my God, that's such a great idea. But I'm not sure if you're going the same way that I'm thinking, are you uploading those images and video to AI and having them point out things to you? Yeah. And you can upload the HVAC system and it'll tell you when it was the brand, the make, the model, the... Like any problems like, oh, this model has had issues or warranty claims or things like that. Wow. Such a great idea. Yes. And there is in the St. Louis real estate community, there's an AI superstar that she just has really opened my mind to using it a lot more on these flips.

37:11And I mean, even things like, hey, can you tell me how many outlet covers I'm going to need? And it takes that video and it tells me how many outlet covers I'm going to need and how many events. It's wild. So just using that stuff to our advantage, it kind of gives you a big brother. It kind of gives you an extra set of eyes and things that you wouldn't catch. So that has really been helpful as well. And we have created just forms that happen on every single property where we walk it and the form looks the same on everything. So we can never go back and say like, hey, we missed this.

37:51Ashley Kehr:So with those forms, are you having it and then you upload the video and then you having AI actually fill out those forms for you? We don't, but that's not a bad idea. That probably could happen, right? Yeah. We kind of have created it off of the inspections, like our occupancy inspections. And we've taken those and just like, hey, what are the key points that we don't want to waste time on? Inspectors come in and look at these properties multiple times, right? That's just time is money in this aspect. So that is what our forms are created off of in order to kind of keep tabs on the things we need to keep tabs on.

38:26But that's really a good idea to use.

38:29Tony Robinson:But when we come back, Molly, I want you to lay out some of the mindset shifts and maybe some of the tactical moves that you say any rookie can apply starting today, including how to deal with imposter syndrome, which you talked about earlier, how to make offers without fear, and how you're involving your kids. Yes, even the three-year-olds in building generational wealth. So we'll cover all that after a quick word from today's show sponsors. All right, we're back here with Molly. Molly, you said something pretty incredible off camera, but that in the last 90 days, Kyle, your husband, has walked 114 properties, made offers on 47 and bought five.

39:04Tony Robinson:That volume is something most rookies would never even come close to. First, how do you think you guys are even getting enough deal flow for him to walk 114 properties? Where are you going to source that volume in such a short period of time? A lot of our properties, surprisingly, are on market. So we have started focusing on on market just because we didn't have a whole lot of luck with the wholesale game. There's just a lot of people trying to be wholesalers and they don't necessarily know the market or they don't live here. And it just makes it a little bit more convoluted. So a lot of the properties are on market.

39:39A lot of them are maybe portfolio loans that other people in the area have brought to us. Some are off market or we've created really great relationships with some realtors in the area and they'll bring us off market stuff or things that they don't think that they're going to be able to put on market or that maybe they've passed from a rental perspective on their side. So that's kind of all the different types of ways we've been getting the deals.

40:06Ashley Kehr:Are you working with an agent that's taking you to all these showings and things like that? Or has your husband thought about getting licensed? My husband has thought about getting licensed. We do reach out to a lot of property owners as well. And I, we just don't necessarily know that we want to, it would be a great cost savings, but we don't want to, don't necessarily want to have to like disclose that we're a realtor on those types of things. So we kind of - And there's a lot of paperwork. Yes. Yeah, it would be helpful. And honestly, like he would be a great realtor because of the, you know, he just has a different eye for things, especially walking this many properties.

40:52I'll never forget when he came home from one of these properties. And he said, he's like, yeah, we walked in this property. And the people that were living there said, you know, there's a flea infestation downstairs. And I was like, oh gosh. And he's like, yeah, the contractor was with him said one time we walked out looking like a strawberry and I just couldn't stop thinking about the bugs and the strawberries. And that's not my lane. I work the finance side of things. He can look at the nasty properties.

41:20Ashley Kehr:Well, I was also curious because I mean, I don't know the split of how many were actually on market, but like that's still a lot of properties for an agent to have the patience to walk through with all of these and, you know, only end up buying X amount out of seeing all of these showings. So are you working with one agent? Are you working with several? And why do you think they're okay with being available to do all these showings and, you know, not guaranteeing that, you know, maybe you'll close, you know, a 10th of them even or less. So several, so every Friday, a realtor in the area sets up kind of a walkthrough of like some on market and some off market about 10 to 12 every Friday and new investors, a lot of them, we have a name for ourselves now.

42:08We used to be the new ones that went and now they're like, oh, if Molly and Kyle show up, they're going to buy all the properties. So we can't offer. But we really get to go and motivate them of like, hey, if our numbers work on this and your numbers work on this, make an offer. And I think that's a kind of, you're going back to mindset is just like, make the offer. And I think a lot of these realtors have realized that, because we work with a few, probably three or four, pretty tight. And I think what has made them okay with looking at multiple properties is they know that when we find one, it's going through.

42:46We do have private money now. So they know that that deal is going to close. And there are also, we're actually closing on a wholesale one tomorrow. And I'm excited for that because I think this guy knows now that you bring us a deal and we'll close it.

43:03Ashley Kehr:I need to look at this to flip this real quick and look at it on the agent side. So an agent is setting up almost like little mini open houses at properties where investors can show up at the allotted times, view all these properties. If you are an agent listening to this episode, what a great idea to build relationships, to network with investors, whether they buy one of the houses or not. That is a great idea. Yeah, we love it. And anytime that a new investor or somebody that's interested tells us, we're like, you need to go to Friday walkthroughs because they at least get you in the mindset and you're getting around the people.

43:42Right. Like, I think I don't remember who says it, but the five people you surround yourself with, you know, like that's the sum of you. And when you're doing that every Friday, chances are eventually, regardless, there are some that have been there for a year that haven't pulled the trigger, but they're going to get there. and because they're surrounding themselves with the people that are making the deals.

44:04Ashley Kehr:Yeah, even just to watch what other investors are looking at, pointing out, asking them questions, like just the networking piece of being a rookie real estate investor attending one of those. And how fun, who doesn't love shopping for houses? It's so fun. I brought my mom one time. She's like, of course, trying to figure out the stories of all these houses. But I was like, mom, are you ready? Wear your boots because you never know what you're going to walk through.

44:31Tony Robinson:Molly, I'm curious though, 47 offers on 114. And you even mentioned you tell the other new investors like, hey, just make an offer. And I think that's where a lot of new investors get stuck is that they see whatever the asking price is and maybe their numbers don't quite work there. So they just kind of walk away. Do you know, just like ballpark, how many of your deals are actually below what the original asking price was? Is it like, 10 % where maybe most of what you're closing is at or above? Or is it like 80 % where the majority of what you're buying is actually below what they initially asked?

45:04Tony Robinson:Do you have just like a rough estimate of what that looks like? 100 % of the offers that we have put in are below asking. And I think that's such an important thing for people to understand. Why is it that so many new investors see the purchase price and feel that that is like the, that it's written in stone. How do you overcome that fear of maybe insulting the seller? That's the thing that I hear all the time. I don't want to insult the seller. So I don't want to go too low. How do you not get too caught up on that? That took a while, honestly. And I didn't want us to create these relationships with these realtors and these realtors are getting cussed out by the seller because they're like, why are you bringing us this offer?

45:48And I tell every realtor or anybody that if they want to see my numbers, I'm going to show them my numbers because numbers don't lie. Right. So I am always willing to show my numbers to show that this is what I have to be at in order to make my deal work. And guess what? I know that probably, you know, 80 % of them I'm not going to get. I know that. But I also know that if they don't have any other offers in the next four months and they're still sitting on market and they potentially don't have another option now, now I'm an option. Right. So they have, there have been multiple situations. We dealt with this on our second deal.

46:35Um, I, well, it would have been our second deal, but it took a while, you know, they came to us and we offered them something and they were like, we can't take this. It was a probate situation. It was, you know, uh, I think a grandfather's house. And they were like, oh, no, we're just going to flip it ourselves. And then three months later, they're like, we can't do this. And so you're still, they're still benefiting. It's a win-win, right? They're still getting money that they need, and we are relieving them of the payment that they can't make. So don't be scared to make the offer and also know that potentially six months later, they could come back to you and say, Hey, are you still available to take this offer?

47:20Because that happens a lot.

47:21Tony Robinson:I'll never forget. I think I might've talked about this in a podcast a while ago, but when I first started trying to invest, again, I was focused on Shreveport, Louisiana. I wrote a bunch of letters and I mailed them all out. And I talked to this lady and she had, you know, her and her husband were retiring and they had like, I don't know, like eight or nine houses they were looking to sell. And at the time, they were just asking too much. And I gave her my numbers, much like you. I walked him through like, hey, here's where it works for me and here's why. And we couldn't agree on a terms. She ended up calling me, I think it was like two years later.

47:51Tony Robinson:And she's like, hey, Tony, I don't know if you remember me. We talked a few summers ago. Hey, I think we're finally ready to meet you where you're at. Now, we had stopped investing in that market. We were focusing on short term rental and other things, so I didn't move forward with the deal. But that was two years later, right? And someone still had my phone number. So you never know just by opening up that dialogue, even if it doesn't close today, maybe it's six months, maybe it's 12 months, maybe it's 24 months from now, but at least you've planted that seed to make yourself an option for them if and when they're ready.

48:18When you brought up the handwritten letters, maybe you're the reason that I did this. I wrote 100 handwritten letters and I sent them out. And the only person that called me off of them. This guy was another investor. And he said, Hey, you must be focusing on pre foreclosures because I've seen your letter at like six of my properties. And I was like, great. And he's like, I just want to let you know, um, you're doing your due diligence and also you have great handwriting. And I was like, okay, so how do I get the deals? and he's like well I get them at auction and I said can you teach me and he said no thanks but I was like the worst like the worst he's gonna tell me is no but I was like he doesn't want me to go because he has competition right like he doesn't want to teach me that and maybe in 10 years when he's ready to retire he'll come teach me and until then I'll try a different route

49:19Ashley Kehr:So he was the one that had bought them, but the listing hadn't been updated. At first, I thought all six of his properties were in free foreclosure. Like, whoa, that's a lot of properties to be doing.

49:34Tony Robinson:And let me just clarify to you for any of the other rookies that are listening. When I say handwritten letters, that batch that I sent out, they actually weren't all handwritten. The letters were printed. I signed my name at the bottom and I hand wrote on the envelopes. Um, so maybe save yourself just a little bit of time.

49:51Ashley Kehr:There's companies that have the robots that look like, that's what I do. I have learned my lesson. It was a good learning experience, but it helped.

50:01Tony Robinson:What it helped.

50:02Ashley Kehr:Well, Molly, thank you so much for joining us today. I can't even tell you the last time that I said, that's a great idea. So many times throughout an episode, but where can people reach out to you and find out more information? Yeah. So on Facebook, just Molly Shepard. And then on TikTok, just real estate Molly and on Instagram, real estate underscore Molly. Well, thank you so much for joining us today. I'm Ashley. He's Tony. And we'll see you guys on the next episode of Real Estate Rookie.

50:29Tony Robinson:Hey, rookies, if you're watching this, we want you to apply to be a guest on the Real Estate Rookie podcast. That's right. Ashley and I are looking for amazing stories just like yours to be a part of our Real Estate Rookie podcast. Now, look, you don't need to be an expert. You don't need to have done thousands of deals. Even if you've done one deal, your story could help inspire the next listener.

50:48Ashley Kehr:As a rookie investor, especially if you just got your first deal, it is all fresh in your minds and you are the best person to tell your story, give your experience on how you got it done to help someone else get their first deal.

51:00Tony Robinson:So head over to biggerpockets.com slash guest if you want to be a part of our show. Again, that's biggerpockets.com slash guest. And we'd love to have you on.

From the publisher

How badly do you want to leave your nine-to-five job, retire early, or travel the world? For this mom of four, working until traditional retirement age was never an option. She’s already taken down eight real estate deals in just two years, which has allowed her husband to quit his W-2 job. And she’s next in line!

Welcome back to the Real Estate Rookie podcast! Molly Shepard is a U.S. Army veteran, busy mom, and full-time loan officer, and yet she’s been able to carve out time to work on the one thing that will give her family financial freedom: real estate investing. Motivated to be work-optional as soon as possible, Molly has walked hundreds of houses, made dozens of offers, and bought several properties in a matter of months.

But she hasn’t done it without help. In this episode, Molly shares how she rapidly grew her investing network, allowing her to find more off-market properties and buy them with as little as $0 out of pocket. She also walks you through the deal that started it all—a home-run house flip that netted her $50,000 in pure profit!

In this episode we cover:

How Molly and her husband flipped eight houses in under two years

Investing in real estate while working full-time and raising four children

How Molly pocketed $50,000 in pure profit on her very first house flip

Creative ways to fund your real estate deals while paying as little as $0 upfront

Crucial details you can’t afford to overlook during your due diligence period

And So Much More!

Learn more about your ad choices. Visit megaphone.fm/adchoices

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