AI Bookkeeper in Your Pocket: Automating Bookkeeping for Real Estate Investors with Jenny Cockrell

Jenny Cockrell (00:00)

I found myself just a little while back in the middle of three flips plus managing my other rentals that I hold. And I was spending like two to three hours every morning doing bookkeeping because everything has to go, like I said, by property, by entity. And then with AI, obviously being very popular, I thought, hmm, let me try to get AI to be my bookkeeper. And that was working a little bit. So I got a little excited.

Issa Hanna (01:58)

Welcome back to another episode of the Real Estate Pros Show. I’m your host, Issa Hanna, and today we have Jenny Cockrell with us. Jenny, welcome to the show.

Jenny Cockrell (02:04)

Thank you.

Issa Hanna (02:05)

Super excited to have you on the show. You have a lot of experience in multiple facets of the real estate industry. You own broke you owned a brokerage, you fix and flip, buy and hold. You name it, you’ve done it in our industry. So for my people at home, give us what your main focus is nowadays and then kind of give us a rundown of a day-to-day in Jenny’s world.

Jenny Cockrell (02:26)

Sure. Well, I, as you said, have experienced many facets of real estate over the last 26 years. And today I’m oddly passionate about something that used to drive me a little crazy as a real estate investor, which is keeping up with my books and my expenses by property, by entity. So, what we entrepreneurs do, we build something to solve our problem.

And then I built it to solve my problem. And then I realized, hey, wait a minute. All my friends, all my real estate investor friends have the same problem. Hey, wait a minute. All my small business owners have the same problem. So I spend my days geeking out on bookkeeping with AI.

Issa Hanna (03:06)

I love that you’ve developed this platform. And as a real estate investor myself, we were talking earlier. I shared something crazy that would have never happened if I had your platform. The platform is called BusiB, you guys. I’m gonna let Jenny take the floor and explain exactly how this thing works to you guys and why it can help your business so much. Jenny, take it away.

Jenny Cockrell (03:25)

Okay, great. Thank you. So yeah,

I found myself just a little while back in the middle of three flips plus managing my other rentals that I hold. And I was spending like two to three hours every morning doing bookkeeping because everything has to go, like I said, by property, by entity. And then with AI, obviously being very popular, I thought, hmm, let me try to get AI to be my bookkeeper. And that was working a little bit. So I got a little excited.

But then I got very upset because it didn’t remember what I said last month. Well, if it can’t remember what I said last month, how’s it going to help me get my numbers right? How’s that going to be accurate? So again, being the entrepreneur that I am, couldn’t help myself, but I geeked out a little bit and I actually built a system. So we actually have a system including secure databases and that sort of thing that manages all of your data.

And the AI is just our conversation piece, our research assistant, that sort of thing. But I no longer need any of those other platforms. I literally pick up my phone, click the app, and say, Hey B, I just spent $78 at Home Depot for supplies on Elm Street. Now it’s classified by the category for the business expense by the property, which is probably tied to an entity.

And it is tax classified. So at the end of the year, when I need to do my taxes, all my transactions have already been classified by type of transaction, which property it went to, which entity it went to. And I’m I don’t have anything to review and do at the end of the year except send it on to my accountant.

Issa Hanna (05:09)

My goodness, you figured out how to how to basically make a W-2 for us, right? For the investors, because we were talking about it earlier. Every year it’s a time us investors dread. It takes hours to do your taxes when you have a lot of properties. Your accountant always charges you tons of money because they’re putting in so much extra hours. So this is not only gonna save you time, it’s gonna save your accountant time, which in return will probably

You’ll be charged less for doing your taxes. Unbelievable. You have a you’ve created a bookkeeper in your pocket. And I wouldn’t put that past you because in our previous conversation, you said you started the first real estate website in your town. So can you give us a little more about that story?

Jenny Cockrell (05:47)

Sure. Yeah. So it was 2000 and I was going to sell my house. And I thought, well, let me rent for a while until I buy something else. And you had to go through the classified in the newspaper. I thought, this is crazy. I don’t have time to call all these people, blah, blah, blah. So I this internet thing was around. I thought, hmm, why doesn’t somebody have all of these properties online that I could look at? Well, they didn’t.

Light bulb went off. So I built the first real estate website in Greenville. And it was it was great because immediately people started finding me, because nobody else had ever built a website for real estate. And I even pitched it to the real estate companies, and that was in 2000, and they just said, no, we’re just gonna keep doing it the way we’ve always done it. So that again gave me an opportunity to build a business.

Issa Hanna (06:38)

I love that. And every great entrepreneur, you read about in books, you do all that, you guys are great problem solvers, you guys are great forward thinkers, you guys are visionaries. So you saw the internet, you saw how much it could bring to the business, you made the first website, you tried to pitch it to the brokerages who turned you down and here we are now. The real estate industry, I’m also an agent, would not exist without the internet right now. Be no way that we’d have to, you know, we’d be able to

Carry books. My generation, we can’t follow a map, we have to put it on the GPS. And now here you are embracing AI, which is in my opinion, in a lot of people’s opinion, larger than the internet. It’s gonna make more millionaires, it’s gonna do more for than the internet. So I do not doubt you’re a great entrepreneur because you you’ve been able to identify

The internet and now AI. You’ve built a bookkeeper in the pocket. BusiB is gonna save investors so much money. But I wanna rewind the clock a little bit. I wanna you kinda touched on it in our pre conversation. I wanna know your origin story. How’d you get into becoming a real estate investor?

Jenny Cockrell (07:40)

Well, it’s actually attributed to like I was saying, I built this website and I built it as a marketing tool for other agents, other real estate companies. And since they said no, we’re just gonna keep doing it the way we’ve always done it, I thought, hmm, no, these people are already coming to my site. So I’ve got to go figure this thing out on my own. So I just went and got my property management license and because I, I really believed in providing services for rental homes.

Every you could get a real estate agent for buying a house, but nobody was helping you when you were moving to an area and you needed a rental. Because in our town we had a lot of corporate people coming in for three to five year stints and they didn’t really want to buy. They just wanted to rent. And, now with the such a mobile society, people like to rent first, before they decide where to buy in an area.

And there just wasn’t any services for that. So I provided the services for that. And then that rolled naturally into real estate investing because then other agents would be calling me asking about rental homes and what they would rent for and all of that. So it just grew right into that. And then my husband was trying to sell his home after his divorce. And I said, you don’t want to do that. You want to rent it instead.

And he was like, I don’t want anything to do with rentals. I said, no, let me explain it to you. So I explained it to him. He’s like, So I rented his house. And long story short, we’ve been married 22 years. I did a good job with his house, huh?

Issa Hanna (09:06)

A hundred percent. I was gonna say you taught him the way, you built him equity. A lot of people have a sticker about renting, especially when the mortgage the property’s mortgaged, especially if it’s their former residence. They don’t wanna rent it, but I tell people all the time, you already got the property, it’s already yours, you’ve already paid it down. If that rent covers the mortgage and you can make a little bit of money off of it, even if it breaks dead even.

I would keep that because as time goes on, you’re having somebody else pay off your mortgage. I joked earlier. I said you must have made him a lot of money over the years that he married you. I would marry my realtor too if I if I she made me tons of money. I want to ask you now about a real estate nightmare, right? We’re investors, we all have them. So give me a time where

You invested in a property and something went south and you had to pivot or you had to just get through it.

Jenny Cockrell (09:55)

Boy, real estate has given me a lot of opportunities there. Actually I can think of one very recently where because now where I live, we have these hundred plus year old homes and they’re beautiful, but they’re old, so they need a complete renovation. And so what I found was there was more structural issues than

My inspection, even though I’d gotten an inspection, didn’t show up. And so we actually were able to pivot by we had to go up underneath the house to secure, the foundation. And in doing so, it was easier to get it through the wall than going underneath the house. So we cut out the sheetrock and the floor and everything to get underneath the house from that direction.

And then we ended up taking that area where we had to cut it out. And then we built in shelves. And this was in a dining room. So we built in shelves with glass shelves. It ended up being beautiful, but it wasn’t my plan. It was a structural need, but it became a visual impact.

Issa Hanna (10:56)

I love that. And that’s the thing about us investors. We get to be in great entrepr entrepreneurs, problem solvers, right? Every day you get something new thrown at you in the real estate world. When you do have that real estate nightmare, it can be something you’ve never encountered before. Structural issues, very, very serious, but we never panic. And here you are, you’ve learned

A new way to attack this structural problem. And now, if you were to encounter this in the future, you’re like, okay, we could just do what we did in this property. So you it just makes you that much better. I always tell the young guys, I say, you never lose, you always learn. I love that. And you are sharing so much knowledge with us just by simply talking, the knowledge is just oozing out. I’m loving it. I want to look forward and go back to BusiB because

It is such a revolutionary software that you’ve created. It is going to help a lot of people. So five years down the line, where do you see BusiB?

Jenny Cockrell (12:35)

Wow. Well, five years down the line, I really hope that there is no investor that is panicking trying to figure out how they’re going to suddenly pull their books together and know all of their income and expenses on one property because that’s what happens. I found out that a lot of us we don’t do our taxes on time most of the time because it’s too much.

But if you have an investor that you’re working with, a partner, you’ve got to have clean books. So I really hope that I’m going to eliminate that problem because the two to three hours I used to spent spend on bookkeeping, I was a lot more valuable out in the field, either looking for another deal, inspecting what somebody else has done. My time was more valuable out in the field, not in front of a computer. And I want to say one more.

More thing about that. You’re supposed to know your numbers, right? Know your numbers is a thing. Like we’re supposed to know where we stand. Well, how many people wake up in the morning and actually know their numbers? Not many. With BusiB, you actually get an email that’s waiting for you every morning that says how much income you have brought in that month, how much more income you’re expected to have that month.

How much your expenses are so far this month, what your bills currently are outstanding for the month, and what your cash position is every morning.

Issa Hanna (13:56)

Unbelievable. It gives you a checklist every morning, you guys. And for people in our world, we gotta learn how to budget our time. Like you said, your time is more valuable in the field, your time is more valuable than crunching numbers. So a lot of times we put it on the back burner or we’ve got so much going on, we just forget. I love that. You it’s a it’s a morning reminder with a checklist. Hey, this is what’s going on in your business right here, right in front of your eyes.

Unbelievable. It it’s truly revolutionary. As a landlord myself, I could see how valuable this software is. And now for our people at home who are excited because like I said, I’m a landlord, you just telling me about this. I’m very excited. So I know my landlords at home are very excited. How could they download BusiB? How could they get a hold of you guys?

Jenny Cockrell (14:40)

Yeah, just go to BusiB.co, BusiB.co and BusiB stands for business bookkeeping. So I just shortened it to BusiB. And you can go there. You can send me a message through I’m actually a human. If you send a message, I’ll get your message. So any they can contact me there. We’re also on Facebook. So if you wanted to send me a message through Messenger on Facebook, you could do that as well.

But I’ll tell you, I used to have on my calendar every day at five PM do your QuickBooks. Every day. Do you think I sat down at five o’clock PM and did my QuickBooks every day?

Issa Hanna (15:16)

Landlords and investors, we are people look up to us, but that’s one spot that I can say a good ninety percent of landlords, they’re not on top of their books. They don’t know. I’m guilty of it myself. You were guilty of it until you solved your problem. So guys

Jenny Cockrell (15:32)

We do have a rent roll in BusiB. It naturally builds your rent roll for you. I used to do your typical spreadsheet, because I tried the software programs and most of them were a little bit more than what I needed for as an individual landlord. So I did spreadsheets. But now BusiB actually keeps the rent roll for me.

Issa Hanna (15:50)

I love that. And another thing that just popped into my mind, you guys who do the DSCR loans and the financing and the flips, they’re always asking you for exactly what BusiB has in it, literally at a tap. So when you are doing these loans and your loan officer is asking you, Hey, let me get the rent roll, let me do this. BusiB has it all in there, you guys. Everything under one umbrella, it’s literally a bookkeeper in your pocket. Truly, truly revolu revolutionary, Jenny. And

I want to leave off with a piece of advice for our young viewers, right? So we have a lot of young professionals in the space, whether they’re realtors, loan officers, new investors. And I want to ask your advice about business relationships growing your network because very important our business, some would say the most important thing in our business. So to the young guy who just got his real estate license, or the young guy who just wants to get out there and start investing, what would be your advice to them on

Establishing that first business connection and starting to grow the network.

Jenny Cockrell (17:28)

Well, there’s this old saying that goes, People don’t care how much until they know how much you care. And that to me means you meet someone and you ask them about them, their business, their issues. Let them tell you what they need, what their issues are, because that is showing that you care. You want to hear their pain points.

And when you hear their pain points, listen for opportunities. Because that is what I focused on my entire career was listening for the pain point opportunity that I could help them. And then because I cared and wanted to know I could solve a problem, now we have a relationship. And once you do that with someone, they love you and they’re happy to tell their friends about you as well. So especially from an agent’s perspective.

That’s extremely valuable, but it’s also very valuable from an investor perspective because everybody’s gonna buy or sell a house at some point, right?

Issa Hanna (18:28)

I love that advice. And guys at home, the ones that watch the show a lot or listen to us a lot. Every major operator, every very successful great entrepreneur gives you the exact same advice almost but in different words. Relationships are built on you caring about that person. They’re not a paycheck, they’re an actual person. So if you care about solving their problems for them, you care about their business, they can see that it goes a long way. And I always say this.

It’s like sprinkling seeds, right? So you treat that one client right or you treat that one investor right, whatever it is, like Jenny said, he’s gonna be happy to refer you to the other people. Everybody wants to have a guy, be that guy. But you can’t be that guy unless you care about the people and you actually come in with pure intention. So I love that. I built my whole real estate career on that exact philosophy, Jenny. So that’s why I wanted to leave off with that advice.

Jenny, thank you so much for coming on the show. It was a true honor to host.

Jenny Cockrell (19:23)

Thank you. I’ve enjoyed it and I love your show. Thank you so much.

Issa Hanna (19:26)

Thank you. And to our viewers at home, if you enjoyed my conversation with Jenny and want to see more like it, make sure to hit like and subscribe. I talk to people every day that can bring us different knowledge on every aspect of the real estate industry. Until next time, the Real Estate Pros are out.