ITF 12 | Exponential Growth


Today’s guest has personally the biggest influence on me – she’s the one that convinced me to get the FI Team started. In today’s episode, Shelby Osborne will also inspire you with her stories and her optimistic attitude.

Shelby Osborne was a US Army captain when she realized she didn’t want to trade her own time for money. So she dropped out of the army, and in just three years, she has acquired over 50 units – and still counting!

She was even awarded the Keller Williams Rookie of the Year. Now, she is the owner of Five Pillars Realty Group and the founder of Pints & Properties!

Shelby is a living “wealth of knowledge” when it comes to real estate investing. In this episode, she will share how she made a brand for herself, her unique BRRRRnB strategy, and why you should learn to develop your personality and not just your investing skills!

Want to pick her brains and learn from her experience? Listen and enjoy the show!

Listen to the podcast here


Zero To Hero: From 0 Units To Over 50 Units Within 3 Years With Shelby Osborne

Nick, how are you doing?

I’m doing great. How about you?

I’m doing good. Some exciting stuff is happening over at my rehab on the last day. We’re about to be done. The contractor was about to leave. The city inspector comes knocking on the door and puts a stop-work order on the window because we went around the rules and did not pull permits. Now that whole process is probably going to be delayed a month or two. If you’re trying to take shortcuts, don’t be like me and pull the permits.

That’s terrible. A similar situation has happened since the last time we talked. The last contractor that I fired never pulled permits. My new contractor came in expecting to see the sign in the yard with everything out there, but it wasn’t there. It only took a week in Alabama, so it wasn’t too bad, but it’s a very similar situation.

It’s tough because a lot of investors out there don’t pull permits because it’s just a quick, easy thing and all that. All it takes is one guy to rat you out and you got the inspector knocking on your door. If you want to play it safe, I will always suggest pulling the permits. We should have a t-shirt, “Let’s pull the permits.”

Enough about permit pulling. We got Shelby Osborne. She was the one that convinced me to start The FI Team. I was out there in December of 2019. She showed me what got her to set up the Five Pillars team and all that kind of stuff. It took a little while to get comfortable with it, but it made perfect sense. She’s helped me out. Her story is incredible. She has gone from basically zero units in 2017 to over 50 now. It shows you that this whole real estate game is exponential growth. You’ve got to keep at it and trust the process.

Her story was awesome. It was inspiring, especially as a previous soldier. The way her real estate investing career took off was great and I’m super excited to talk to her.

Let’s get her on the show.

Welcome to the show, Shelby. How are you doing?

I’m doing well. Thank you so much for having me.

Thank you for coming on the show and taking time out of your busy day. It looks like you’ve got this aura of light behind you. That’s probably just you.

We can get right into it here. We usually start this thing off by telling us a little bit about how you got started in real estate, tell us a little about yourself, how you heard about financial independence, and go from there.

A little bit about myself. I was in the army for six years and got frustrated with the normal things that people get frustrated with being in the military, like inefficiencies, frustrations with lack of communication, last-minute planning pushed aside for whatever is the hot, shiny ball of the moment. I was like, “I’m not going to do this.” I want to stop trading my time for money. I want to find a way that I can make money in my sleep. That led me to real estate. After some time on Google, I discovered BiggerPockets and Robert Kiyosaki, although it was not Rich Dad that brought me on this. It was The Business of the 21st Century, which surprises everyone.

I was like, “Real estate is what I want to do. That way, the rent checks can come in even when I’m not working,” type of thing. When I made that decision, I was like, “I’m going to get out of the army.” I dropped my paperwork to get out of the army. I went to night school to get my real estate license because I decided that that was the best way to be super involved in my market, get deals, and negotiate for myself. I didn’t do one deal with an agent before I was licensed and was able to represent myself. I was like, “Holy shit. I can do that better.”

Did you discover financial independence while you’re in the military and that’s what made you want to leave or did you leave and then discover it?

While I was in the military, I wouldn’t even call it a clearly defined financial independence. I was like, “I know I don’t want to trade my time for money.” To do that, I want to not have to think about money, which in essence, is financial independence. I just didn’t call it that.

Financial independence is not spending your time for money, not having to even think about money. Click To Tweet

You had the theory, but you didn’t articulate it and put the words to it. You had it in your head.

Now, I feel like it’s everywhere. When your world is focused in one direction, you see things within that scope. When another idea sparks, you suddenly see all the opportunities within that new spark. Here you are finding out. At the time, I wasn’t surrounded by it and now it’s all I see and all I hear everywhere.

That’s a huge way to make that shift. It’s to surround yourself with it, then naturally, it’ll come and opportunities will fall your way. Let’s try to get a little bit of a timeline. A lot of people reading the show are just getting started and they want to see what it takes to go from zero to hero. What year did you leave the military?

I left the military in January of 2018.

I thought you were out for a while.

No. I’m still fresh to death.

You left the military and you had zero rental properties at this time. Was that your ground zero?

No. I had technically three doors by that time because in my first duty station when I was in the military, I bought a condo with my VA loan to live in and then started renting it out when I moved, which was completely inadvertent. I never ran numbers. I fell into an amazing cashflowing property that’s increased $100,000 in equity. That was in Washington, though. It’s very different. I had the spark in April of 2017 and I bought my first intentional investment property in November of 2017, which was a duplex that I bought conventionally because I didn’t know about any other strategies. I was like, “25% down, sure.”

Run us through that deal and those numbers because the first one is always the scariest. Let us know the feelings you were feeling and if you had any emotions.

I ran those numbers a million times because I was like, “Is this banging deal. Why has no one bought it? Am I crazy? What am I missing?” The market was very different now. It’s saturated. Everyone wants to invest in a vehicle. At this time, in November of 2017, it was a duplex and it had been on the market for 74 days. It was listed at $90,000 and it was rented for $550 on each side. I decided, “I’m going to lowball.” I told my agent I wanted to lowball at $75,000, $15,000 under and he’s like, “You shouldn’t do that.” I was like, “Do it,” and it got accepted. It was $75,000 at $550 on each side. They rent for $725 on one side and $675 on the other. It’s nice. I’ve been increasing it every time because they were under market rent at the time. I pushed my limits over here. That’s it.

You’re at the 2% rule there or close.

It’s almost there. It’s beautiful. Especially when you put 25% down, your numbers are trough level.

That’s some amazing cashflow for sure. At that price point, heck yeah.

My mortgage is $424 a month.

Your cashflowing over $1,000 over the mortgage?

Pretty much. It’s quick cash.

ITF 12 | Exponential Growth
Exponential Growth: Getting FI isn’t just about hustling. That alone isn’t enough. You need self-development and be able to read people. You have to do what you promised you were going to do.


Do you put aside anything for reserves or anything like that?

When I’m running my numbers, I do it in a traditional BiggerPockets way where I put 10% capital expenditures, 5% maintenance, 5%, vacancies and 10% of property management. I said that all weird, but you guys get the point. When I buy the property, I don’t take part, put it in a pot, and take my other cash. I don’t do that. I shove it all into one pot, which is my reserves, until I build up to where I want it to be and then I start taking all the cashflow on after that point.

That’s Scott Trench. If you guys know who he is, he does a similar method where he takes $15,000 for his first property then $10,000 for everyone thereafter. The numbers can change based on your market in different situations, but whatever makes you feel comfortable. That’s awesome.

That was the timeline. After I got out in January 2018, that was my first year in real estate and I was the Keller Williams Rookie of the Year for all North and South Carolina as an agent. I acquired sixteen by the end of my first year.

What did you do to become Keller Williams Rookie of the Year? Maybe some agents are reading this, so give them some tips.

It was all volume. I closed 48 in my first year as an individual agent. I like to be busy.

How did you get your leads? How did you generate all that business being the new kid on the block?

I used to use all my army resources. I would not shut up about getting into real estate on my way out. I was the finance and HR for 750 men units on Fort Bragg. I had a lot of connections and many other people in HR positions, and I made sure that it got out. Also, people were in processing my unit and I had business cards. My soldiers, because I was the OIC, they gave everyone my business card. I was shameless.

It’s like a no-fuck given approach.

That helped but also, I had a couple of contractors with who I was good friends with. I pinpoint the people who will talk to anyone. I make sure that they love me because then they won’t shut up when they’re out doing around and stuff like that. I got so many leads from one particular contractor that first year. I also started Pints & Properties. It’s a real estate investors’ Meetup that’s free value to whoever. Anyone interested in investing, house hackers in particular at Fort Bragg, and that all spiraled.

Meetups are a super powerful way to generate leads. Darren Sager, who’s my mentor, has a big Meetup in New York and crushes it out there. People in Denver here do Meetups and it’s a phenomenal way. You’re crushing it by straight-up hustling and no sleep, no life for one year, which everyone should do.

When your world is focused in one direction, you see things within that scope. When another idea sparks, you suddenly see all the opportunities within that new spark. Click To Tweet

A lot of it comes through self-development. You have to be able to read people. You have to be able to talk to people. You have to do what you promised you were going to do. Hustling alone isn’t enough. Read the right books, implement immediately, take action and do what you’re supposed to do. It makes people like you. I talked about that with my agents. I’m like, “Be more likable. People who buy from you like you.”

Being consistent with it, too, is what I found. There’s a lot of people who will be intense and do all this stuff for two weeks because they get excited about it, but then they drop off. That doesn’t do anything except waste two weeks.

It’s all about that consistency, for sure.

I heard a quote, “Consistency trumps intensity.” It was my favorite quote. You’re crushing the agent game. You’ve got a decent number of commissions through that. Did you funnel everything you made into rental properties? How did you go from 3 to 16 based on your first year?

I did it a bunch of different ways. I bought a quad with my VA loan, which I won’t even go into and I house hacked that. That was four more doors. By the way, I’m counting doors. I’m not talking about individual properties. I have a quad by this point. At that moment, I did not have my every two-week paychecks coming in and no one was going to lend to a brand new real estate agent. I was like, “I have to keep buying. How am I going to do this?” That’s when I started getting to private money, which I’m big on. I still use a lot of it now. I use private money to fund a single-family foreclosure after that, an off-market duplex and a six-unit apartment complex. That adds up to sixteen.

I love that relentlessness. A lot of people would say, “I can’t buy property for the next two years because I need those two years of tax returns.” In order to be successful and to get there as fast as possible, you did the whole Rich Dad Poor Dad thing. You didn’t say, “I can’t do this.” You said, “How can I do this?” Private money seemed to be the obvious step. How did you go about raising private money and all that?

It’s not easy. It takes a lot of uncomfortable phone calls and conversations. When you are a newer agent, investor and all that stuff, it is hard. All my people came ultimately from my sphere of influence or my sphere’s sphere. Ultimately, it boils down to who knows me, likes me and trusts me, most importantly because I’m not even selling them on my experience or all this amazingness. It’s like, “I know Shelby. She’ll do what she promises she’s going to do,” which scares a lot of people and rightfully so. That’s what I did. We did promissory notes, liens against the property. Everything was done through an attorney and it was secured. That’s how I raised private capital.

It sounds like it was mostly debt.

They are BRRRR deals. The cool thing about it, too, on my private money, it was interest only with a five-year balloon is essentially what I did. I would give them the option after my completion of whatever project it was because there were no payment penalties written into the note. I was like, “We completed this project. Here’s your entire money back if you would like it.” Every single time, they’re like, “No, keep it. Roll it into the next project.” It’s been successful in that way.

We had a couple of terms here that some people may not know if they’re not in the finance world, balloon payment and pre-payment penalty. We can maybe first go into describing the partnership. What’s the difference between a debt partnership and an equity partnership? The difference between a debt partnership and an equity partnership is when you have an equity partnership, it’s saying, “Shelby, you and I are going to go into a deal together. We’re going to buy this house together. I’m going to give you 100% of the money. You’re going to do 100% of the work and I’m going to do nothing and we’re going to still own that property 50/50. Any proceeds that come into that property, we split 50/50. When you sell it, it’s 50/50.”

That’s how an equity partnership would work. It’s a little bit more, for lack of a better word, in bed together. We’re married to each other for this deal. Debt partnership, on the other hand, is like, “Shelby, I’m going to give you $100,000. You give me my 10% interest-only payments over the course of five years.

At the end of the five years, that $100,000 will be due on top of any unpaid interest. Once you put me back in my principal, we both go our separate ways. That’s the end of the deal.” I like doing debt partnerships a lot more than equity partnerships because it is cleaner, but some people love equity. The fewer people involved, the better.

That is what we’ve been doing a lot of. It’s great because when you’re using people in your sphere of influence who are necessarily very accustomed to the real estate world. You can make things happen that make both parties happy without knowing, “If people knew all about this hard money, rates, terms, and all that stuff.” The private money rates that we give are very good. Don’t get me wrong, but it’s still beneficial to both parties.

Is that what you did for all those deals there in 2018?

Besides my quad, yes.

Probably the best way to do any deal is to house hack. Did you get a different color? I might need to steal one of them. You had a hell of a year in 2018. Keller Williams Rookie of the Year, 3 to 16 units, 40-something deals closed. It’s an incredible year. What happened next?

ITF 12 | Exponential Growth
Exponential Growth: Hustling alone isn’t enough. Read the right books, implement immediately, take action and do what you’re supposed to do.


On the agent side, we created Five Pillars Realty Group. Our first year was 2019 and we closed $130,000 as a team in the first year which I was happy about and then in 2020, we’ve closed $145,000 so far.

What prompted you to start the Five Pillars team and how did that come about? How did you find your people, your partners there?

It’s funny because when I was in the army, I specifically remember saying, “I do not want to create a team. I want to work by myself, so the agent only worries about me.” I know you know this about being in the military. When you’re responsible for people, you’re also responsible for their problems, and soldiers can be challenging to say. I had no intention of creating a team, but there was such an influx and traction on my business that I had to grow because my customer service was lacking. It would take me three days to reply to anyone because I didn’t have enough time in the day. I was like, “I refuse to do this. It’s time to grow and improve my life as well so I can have one. I had a TC first and I had an admin assistant. I had Michael Glaspie, who was my first agent who’s Craig’s agent here in Fayetteville.

I work with the Five Pillars as well, full disclosure. They do good.

Thank you. Mike was even a client of mine. It was clients of mine who saw what I was doing and were interested in also investing we’re like, “Let’s do this together. Let’s go.” The majority of my agents are military and investors first and then agents second, which is helpful in our tempo, mindset and communication. All that stuff is helpful to ramp up and build the business in a way similar to how the military operates. We have an HR section and a lead administrator in charge of our other administrators.

It makes sense to grow like that. That was that side of it. In 2019, I started doing more deals with people. Mike, Dan, I, and one other person bought 21 units. I was a pentaplex, 4 duplexes and 2 quads. A couple of more private money BRRRR deals and a duplex. We got into Airbnbs and we’re still into it. The BRRRRnBs are my thing.

I saw that somewhere on BiggerPockets or something. Shelby has got a wealth of knowledge. Let’s dive into the BRRRRnB because that’s something that people probably don’t know too much about.

Does your audience know what a BRRRR is?

You can go ahead and explain it.

It’s all over BiggerPockets. It’s when you buy a property that’s generally in shit condition, you then rehab it, rent it, refinance the property and repeat the whole thing. You’re able to turn your money into multiple deals with one fixed amount of money, which works well when you’re using private money. The difference with the BRRRRnB is that instead of renting it as a long-term buy-and-hold property, you are Airbnb-ing your property. In our market at least, the income that you can make from an Airbnb is significantly higher than you can for the long-term.

The one that I did for the BiggerPockets projects, the long-term rent would be around $950. It was grossing $2,700 consistently, which is awesome. I have a lot more expenses than I would on a long-term buy and hold. The property management fee is higher, but I would still net around $1,000 to $1,200 off of that property, which normally you wouldn’t.

Otherwise, you’d get $900 before rent and then $1,000 right after property management. What does that process look like? Whether it’s a long-term rental or Airbnb, the rehab is a rehab. That’s probably about the same, but how about furnishing the place?

If you do it on your own, it is very time-intensive and stressful. I am all about outsourcing and leverage. I partially did it once and I was like, “I will never do that again.” What we’ve done is we’re in real estate and I contacted one of my stagers who was like, “I’m going to give you a list. Can you furnish this entire thing, start to finish, all of it?” She has grabbed that and made herself an entire business out of it, which I’m so proud and she’s killing it. It’s awesome.

After the rehab is complete, it’s turned over to Amanda Garcia. She has her own onboarding list now for clients to come on. She furnishes the whole thing, including delivery setup, every piece of the puzzle, every spoon, every spatula in the kitchen, three sets of sheets, three sets of everything that you need. It’s ridiculous.

From that point, we turn it over to our property manager. I’ve taken myself out of it. We’re looking at roughly $8,000 for a 3-2, including Amanda’s fee. It’s anywhere from $8,000 to $10,000. It will also range in whatever you guys want, though. If you have uppity taste, cool, but I have her on Facebook Marketplace for a deal.

You probably run the numbers. It costs you an extra $10,000. How long does that extra income take to pay you back? Maybe it’s a year or two.

In the military, when you're responsible for people, you're also responsible for their problems. Click To Tweet

If you don’t want to do delayed financing and if you can wait until six months and you can cash out to include the amount that you put in for the furnishing, if your numbers work, then you’re good.

Have you noticed any down take on Airbnb with the whole COVID situation and all that kind of stuff going on?

It’s hard to answer that question because the majority of Airbnbs went up in October, November, December of 2019. When you first start in Airbnb, our property manager at least, it usually starts the rental rates low because they want to have people in there who see this amazing value and leave all these great reviews. Once the reviews stack up, then they’ll increase the price so that way, it’s fair for what they’re paying for. My whole point for that is we were getting ramped up at the time when COVID was coming in, so it’s hard to tell, but it’s been amazing. I don’t know if COVID has affected it at all, but no issues and almost fully booked. I’m fully booked on the one from the BP thing up through the end of November 2020.

You got that whole Airbnb set up. I’m sure you did the process yourself. I love what you did there. You said you’re never doing this again. Although you maybe didn’t write it out on a chalkboard, if you did, you’d say, “These are the checklist things that we need to do for an Airbnb.”

It’s straight out of The E-Myth if you’ve heard that book. We outsource it or automate each individual thing. That’s how you create a system and that’s how you systematize anything. If I know anything about Shelby, I know she’s got a checklist probably with Amazon, Home Depot and Lowe’s for everything that she wants. She has control of the process, but she doesn’t have to do the process, which is an amazing thing about you.

I love that you know that about me, too. That’s the only reason why Five Pillars has been able to grow at the rate that it has on my investment side. It’s because I believe that I will only do something once. In my emails, if I take a long time to draft an email and think it through, it’s saved as a draft forever and I will never rewrite it. That’s how I created all the things for my agents as well. They have so many freaking email templates for any situation as a buyer or with dealing with a listing that they don’t have to think through. You just fill in the blanks.

I’ve adopted that from you when we had our little powwow back in December. We’re here at the end of 2019 in our journey. You did 130 deals, right?

No. That’s 41 doors by the end of 2019.

You went from 3 to 16 to 41. If you’re in a more expensive market, getting 41 doors is going to be harder than if you were in a $90,000 market. Don’t be flabbergasted by the number of doors. Think about the trajectory of growth. It’s not linear. People say, “I’ll just buy one a year for 10 years.” That’s a good way to think when you start just to get you started. You’re going to end up buying 1 the first year, maybe 1 the second year, then 2 the third year, then 4 then 8 then 16. Before you know it, you’re going to likely have a multimillion-dollar net worth by that ten-year period where you thought you’d only have ten properties.

At least that’s how it’s worked with every other investor that I’ve ever talked to. That’s proof right there. End of 2019, now you guys have legitimatized the Five Pillars Realty Group. You’ve probably made a pretty good brand and name for yourself out in the Fayetteville areas helping out investors. I don’t even know much about 2020.

In 2020, I looked at my buy and hold. We have ten more doors, but I’ve also done three flips. Until 2020, I have personally not done a flip. They’re fun. I don’t know how the market is in Denver due to COVID and stuff like that, but properties are flying off the market. We used to be in a market where it was a buyer’s market and the property would sit. The seller would end up paying $1,000 in concessions and now all our listings are selling for over the list, zero seller concessions. These are amazing offers. I’m glad that I finally started getting into flips.

How does that affect the buy-side of the flip?

For our properties that we’ve done so far, the way that it’s shaken out is of those 10 doors, 2 are courthouse foreclosures. We love our courthouse foreclosures. What we do is our courthouse does not feed our MLS. We have developed a system. Daniel Kidd spearheaded this. Shout out to him. What he did is he went to the courthouse and figured out this archaic, terrible process to check the courthouse properties because they don’t even list it by property. It’s a file number. You have to pull it, go, walk and all these things.

We’ve developed a checklist to do it and now we’ve created an off-market MLS essentially where we hang our wholesale and courthouse deals. We have an intern who now updates it. Anyway, the point is that those properties were not on the MLS. They were from our courthouse foreclosures. The eight-unit that we closed on wasn’t MLS property, but it was a distributor. We ended up lowballing it and getting a deal out of it. Our flips are courthouse as well. Courthouse foreclosures are the shoot.

Courthouse foreclosures are great in those cheaper markets. People come up to me in the Denver market and say, “I want to buy a foreclosure.” I’m like, “A bank’s probably not going to traditionally lend on it. You’re going to have to pay any fees that are outstanding.” Sometimes, I don’t think a newbie should be getting into foreclosure because there are so many unknowns usually buying it as is. If you’ve got $20,000 or $30,000, a foreclosure is probably not the way to go because there’s likely something wrong with it. Prove me wrong. Maybe I’m wrong.

It’s probably market-specific because I love foreclosures, not only the courthouse ones. The courthouse ones are way riskier. We have a ton of VA-specific foreclosures because we’re right by Fort Bragg. People will buy homes and foreclose on them. Those tend to be amazing deals in this market because the house often isn’t even trashed and allows for inspections. If you do back out, you can get your earnest money back. I’m sure it’s market-specific, but be careful.

ITF 12 | Exponential Growth
Exponential Growth: My why is now to bear greater responsibility and to impact in a positive way those people in my life and build something worth the time and effort.


I wouldn’t do foreclosure on your first deal, but as you start getting a little more experienced, you start having some more money and you can absorb any mistakes you may make. It could happen. For example, I did one of the foreclosures over there at Fayetteville. It was $82,000. I probably should have done my research better, but there was $8,000 and some backups paid off. I have some liens on the property I had to pay off. It’s another $8,000 that I didn’t realize, so I was like, “The deal still works, but it’s not as good as I thought it was.” If you can’t stomach an $8,000 blow, then you might be screwed.

It’s such a good point, too, because real estate is not perfect and it’s not pretty. There’s not a single thing that ever goes as planned. If you’re not mentally prepared for more than one bump in your road and big bumps, then maybe it’s not right for you.

You must expect the bumps. Put on your suit of armor and take the blows.

For the courthouse foreclosures, are you typically paying cash for those? Can you use hard money for those? I’m thinking of more expensive markets.

It depends. When we first asked the courthouse, they said it must be cash. Of course, there are lots of things that act as cash and that we’ve had no issue closing. Some people use cash. A lot of people use lines of credit. Before COVID hit, it was very easy to get $75,000 lines of credit at one of our local banks. If you set that up before COVID, you have this line in $75,000, which will go a long way. People have been buying it and that method. Also, hard money. Although technically, if you ask for hard money like, “We’re going to do this,” they’re probably going to be like, “Yeah.” Not that I’m saying never lie to your lender. I’m saying that there are ways to make things work.

It’s all about thinking creatively. Shelby, we have taken up a lot of your time. We appreciate it and love talking to you. We can probably get into the final part of our show, The Final Four.

Shelby, what is the book that you’re reading right now?

Jordan Peterson’s 12 Rules for Life. It’s not all real estate. My thing lately is not real estate. I love real estate and I’m still in it every single day, but what I’m interested in are big psychological questions. I love what I’m reading right now. It’s very good.

I’ll check it out. Sometimes it’s good to take your mind off real estate once in a while.

I started listening to his podcast. I think it’s about that. You shared it, Shelby. I was like, “I want a new podcast,” so I listened to that.

I’m addicted. It’s so good.

I’ll be checking it out for sure.

What is the best piece of advice you’ve ever received?

“Find a way to win.” When I was a second lieutenant, my old brigade commander would say that all the time. I love it so much because if they say, “No, we won’t give you a loan,” there’s a way to find it.

Felipe Mejia, the guy on the BiggerPockets Rookie Podcast, has an episode that says anytime he gets a no, he says, “Yes, why?” That’s a cool thing to do because then at least you understand why they don’t. You can either address that reasoning or find someone else who doesn’t care about that reason why. It’s huge.

What is your why?

Do what is meaningful and not what is expedient. Click To Tweet

That’s changed so much. It started that I wanted to go and travel the world and never have to answer a phone call. Just go, explore and live life. Now my why has shifted to doing what is meaningful and not what is expedient. That’s a quote from Jordan Peterson. My why is now to bear greater responsibility and to impact in a positive way those people in my life and build something worth the time the effort.

That’s the thing, too. Your why always change as you progress in your real estate career or whatever it is in your life. It always changes. There’s always something different. I love your input.

As you mature and grow, it changes. Do you put pineapple on your pizza?

Hell, yeah.

Me too.

That’s a question we asked before you’re on the podcast to make sure only pineapple-on-pizza lovers are on the podcast.

I love that you guys don’t send any read-ahead. This is all just whatever comes out of the mouth. It’s great.

Shelby, where can people find out more about you if they want to reach out?

I’m on Instagram, Facebook and Instagram is @RealEstateWithShelby. Message me.

Shelby, thank you so much for coming to the show. You’ve enlightened a lot of our readers. Hopefully, they can take some action and find a way to win.

Thank you so much for having me. It was so much fun.

We’ll see you soon.

That was Shelby Osborne. “Find a way to win,” and she has done that quite a few times.

I love that quote. I’m going to start using that.

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Maybe create another t-shirt.

We can create multiple t-shirts after that interview. She was awesome. During the interview, she had plenty of information. I love her way of creating processes and making things seem so easy. Doing one thing one time and then passing it off, making systems and stuff. She was an awesome person to speak with.

Systems, checklists is all it is. If you think about it, guys, a system is a checklist. Think about how the system is created. You have a process you want to do. You have a step-by-step checklist on how to get it done, then you either automate or outsource it. Once that all the steps are completed, you’ve got yourself a system where you’re not doing any of the work and it’s just flowing on its own. She’s done that multiple times throughout her investments and her agent business. It’s proven to be fruitful for her and how they can grow.

It was an awesome interview. I’m looking forward to talking with her in the future.

She’s crushing it and maybe we’ll live up to her hype.

I hope so because she is killing it.

I know you’re heading out to the mountains, so enjoy yourself out there. Be careful of any of the wildfires and bears. You’re going to Glenwood Springs, which is where the fires were happening.

The fires were within a mile from this cabin. There are 6 or 7 of us families going out there, all military friends. The fire was so close. We were worried that it was going to get canceled. Luckily, it didn’t. We’re going to be out there, so I’m looking forward to it. It’s going to be fun. Have a good weekend, too. You enjoy your time.

I will do. We’ll see you in the next episode.

Talk to you soon.


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About Shelby Osborne

Shelby graduated from the University of South Carolina in 2012, served in the Army for 6 years and got out as a Captain at the beginning of 2018 to dive into Real Estate full-time as both a broker & investor in Fayetteville, NC.

Following her first year as a broker, Shelby was recognized as the Keller Williams Rookie of the Year for the “Carolinas Region” (all of North & South Carolina) and began to expand, creating her own team of real estate professionals. Five Pillars Realty Group became official in 2019 and expanded to Charlotte, NC in 2020. Both Fayetteville & Charlotte offices specialize in helping military and investors nationwide meet their goals. “Pints & Properties,” their Real Estate Investors meetup, is booming & continuing to grow rapidly.

Meanwhile, Shelby was relentless in growing her rental property portfolio. Since purchasing her first intentional rental property in November 2017, she now owns 74 units, acquired using several different strategies and comprised of a little bit of everything: single-families, residential multi-family, commercial multi-family and short-term rentals… plus a bit of Airbnb arbitrage.

Between CEO duties and continuing to invest, Shelby operates “Pillars Consulting” – a company designed to transform Real Estate Brokers into their full potential — and “Life & Lens Photography” — a company designed to showcase Multi-Family Syndication projects and help investors raise private capital.


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