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Real Estate Pros · March 24, 2026 · 25 min listen

From Loss to Power: How Bobbie Evans Built a Real Estate Business Through Demolition and Investing

With Bobbie Evans

Show summary

In this episode, Bobbie Evans shares her journey from demolition services to successful real estate investing, highlighting key strategies, challenges, and her inspiring story of resilience and growth.

Key takeaways

  • Bobbie's demolition and bulk trash removal company, Pick It Bare, holds contracts with property management companies and large clients like Amazon, which puts her in front of people giving up homes before those properties ever hit the market.
  • Her first solo real estate project was in Baltimore County: she purchased a property, fully rehabbed it while acting as her own GC, rented it out for a period to gain landlord experience, then listed it and had it under contract within 60 days of listing.
  • She chose to stay close to home (Baltimore County) so she could personally oversee the rehab and coordinate tradespeople directly rather than hiring a GC, leveraging her construction background.
  • Unplanned expenses can derail a rehab budget — she specifically cites a tree root system that grew into the plumbing as a costly surprise that wasn't accounted for in her loan, and recommends investors inspect for trees, roof condition, and similar hidden issues upfront.
  • She found her first deal through a realtor contact who called her about a estate clean-out after a homeowner's sister passed away; by being the first person in the door before the property was listed, she avoided competition and was able to negotiate directly.
  • On distressed sellers: houses can go into foreclosure over something as small as an unpaid water or tax bill, even on a paid-off property with high equity. Investors can offer to pay off the bill, structure a subject-to deal, or offer a portion of the property's value as a clean, fast exit for sellers who are emotionally done and just want out.
  • Her next moves are scaling from single-family rehabs into Baltimore City multi-unit properties, and eventually into ground-up new construction; she has asked friends to let her shadow them on a project (offering to fund it herself) but says they've declined because they believe she can already do it on her own.

About Bobbie Evans

Bobbie Evans runs Pick It Bare, a bulk trash and demolition removal company based in the Baltimore area with contracts including property management companies and Amazon. She recently completed her first solo real estate project — purchasing, rehabbing, renting, and now selling a property in Baltimore County — and is a widow who has run her business while raising three children.

Listen to the audio

“I found strength within myself that I never knew was possible and I thrived.”

Bobbie Evans

“Consistency, consistency, like just showing up... that consistency eventually paid off.”

Bobbie Evans

“Nervousness and excitement look very similar, Bobbie. They feel the same, but they're very different. So you're not nervous, you're excited.”

Bobbie Evans
demolition servicesbuy and hold investingBaltimore CountyBaltimore Cityestate clean-outssubject-to dealsdistressed sellersself-GC rehabscaling to multi-units

Questions answered in this episode

How did Bobbie Evans get into real estate investing from a demolition business?

Her company, Pick It Bare, does bulk trash and demolition removal with contracts tied to property management companies and large clients like Amazon. That work puts her in contact with people who are giving up homes through foreclosure, estate situations, or hoarding cleanouts, often before the property is listed, which gave her a direct line into finding her first deal.

What was Bobbie Evans's first solo real estate deal?

She purchased, fully rehabbed, and rented out a property in Baltimore County, acting as her own general contractor by coordinating tradespeople herself. After renting it for a period, she listed it and it went under contract within 60 days.

What unexpected costs should investors watch out for in rehabs?

Bobbie points to a tree with a root system that grew into the plumbing as a major unplanned expense that wasn't factored into her loan. She recommends checking for trees, roof damage, and similar hidden issues before buying, since these costs aren't always covered in the financing.

How can investors approach sellers in foreclosure over small debts?

She explains a house can go into foreclosure over an unpaid water or tax bill even when the property has significant equity and no mortgage, if the owner has no income to pay it back. Investors can offer to pay off the bill and structure a subject-to deal, or offer the seller a portion of the property's value for a clean exit if they just want to walk away.

What is Bobbie Evans's business called and where does she operate?

Her company is called Pick It Bare. She currently invests in Baltimore County and is looking at multi-unit properties in Baltimore City for her next project, with a longer-term goal of getting into ground-up new construction.

Resources and links

Full transcript

Bobbie (00:00)

I buried my husband six years ago and I’m a widow and I just remember the feeling when that happened that my whole world had kind of

crumbled around me and what I knew wasn’t going to exist anymore. had been married for 20 years, my entire adult life. And that person that I was when he passed away is nothing like the person that I am now. I found strength within myself that I never knew was possible and I thrived.

Michelle Kesil (02:00)

Hey everybody, welcome to the Real Estate Pros Podcast. I’m your host, Michelle Kesil, and today I’m joined by someone I’m looking forward to chatting with, Bobbie Evans, who does demolition services as well as buy and hold investing. So excited to have you here today, Bobbie.

Bobbie (02:21)

Hi Michelle. I’m very excited to be here. I’m very excited to chat about this. It has a lot of passion in my life right now, so I’m excited to talk about

Michelle Kesil (02:24)

Awesome.

Great, let’s dive in. First off, for those not familiar with you and your work, can you share what your main focus is?

Bobbie (02:39)

My main company we do bulk trash and demolition removal I have some contracts with multiple Property management companies as well as companies as big as Amazon We still service, you know our day-to-day customers for even just one item It puts me in a unique position to be introduced to people who don’t have the means to keep their houses anymore or you know are getting rid of them through various ways, so

My main job also introduces me into the real estate world.

Michelle Kesil (03:12)

Awesome. And as far as investing, what does that look like for you?

Bobbie (03:16)

just put my house on the market less than 60 days ago and it is already under contract so that was already exciting. This is my first alone project that I did beginning to end with ⁓ you know purchasing, fully rehabbing the property. I rented it out for a little while just to have that experience under my belt and now we’re into the final days of selling it so this is my first.

beginning to end alone project and it was a very successful one. So it is been a great experience for me.

Michelle Kesil (03:50)

Awesome and what markets do you operate in?

Bobbie (03:55)

⁓ I bought this in Baltimore County. stayed close to home and that way I could babysit the property and GC myself. I didn’t hire someone to GC the project. Being in the construction world, I felt that I could work with all the different tradesmen myself and get everybody together in the same pH as long as I was in the same neighborhood, not really running too far away for it. So right now Baltimore County.

My next property will probably be Baltimore City. I’m looking there at several right now, some multi units.

Michelle Kesil (04:31)

Awesome. And so what would you say have been some of the main keys that have allowed your business to be able to grow and run smoothly?

Bobbie (05:30)

Consistency, consistency, like just showing up. mean, when it comes to consistency, when you are present over and over and over again, you put yourself in positions and places that people expect you to be because you’re consistent. So when they need you, you’re right where they found you at. I showed up to the same meetings every single Friday. was literally a free lunch.

And just by putting myself in that room consistently, time after time, I met various people from people that have law degrees that were helping me decide what I could and couldn’t do to people who did rental inspections to different situations. But consistency of putting myself in the right places time and time again, even when it was hard and seemed undoable, you know, I still showed up and just continued to put one foot in front of the other consistently.

all the time and that consistency eventually paid off.

Michelle Kesil (06:30)

Awesome. What has been like the biggest challenge you’ve experienced in real estate?

Bobbie (06:36)

Gatekeeping. You know, I was very lucky to have a good group of people around me who were able to guide me into the right areas. But there is no like one place where all of this information is available. So you kind of have to learn as you go. And having some really good people in my corner.

who were able to guide me in the right ways saved me a lot of time and effort in places that I would not have understood with rules I didn’t know that I needed to play by. Whether it was getting rental inspection licenses to even lead paint licensing. It’s kind of like you get into one thing and then you find out you need another thing. I was a lot more prepared than most people would be just by putting myself in those very rooms.

to have that information before it was even necessary. But had I not done that, I could have definitely been in a very bad position several times. I just got very lucky. This project that I just did, I had an amazing experience. And I do know from being around a lot of other people, that is not always the case. You know, there’s a lot of things that I missed or deterred myself from having.

know, critical failure on just by being around a lot of other people. And finances, you know, I didn’t, wasn’t all the way aware of the different things that can come up along your projects when you’re doing these large projects like that. So it really makes a difference that you have some type of buffering behind you when it comes to these type of projects. There were a few times where I almost, you know, threw in the towel that

You know, there was a tree in the yard that grew into the plumbing and the root system and like these are unexpenses Expenses that you just don’t you can’t always know, you know, you go in you kind of roll the dice a little bit and You learn as you go some of the things that I’ll look forward to this time. I Learned as I went, you know, looking for the trees looking for the roof looking for damage. That was before

things that could cost major, major amounts of money that are usually not planned into your loan and stuff. So that was one, definitely, of my learning curve things that I kind of learned as I go now.

Michelle Kesil (09:12)

Yeah, absolutely, that makes sense. And so how did this job help you with your first property? How did the skills transfer?

Bobbie (09:59)

as I said in the beginning, I’m in a very unique position with my main job where I am introduced to a lot of people that are in, you know, peculiar or just very different situations, very difficult situations. You know, I don’t think people ever intend to purchase a home and lose it. And then the embarrassment or the shame that comes with losing something like that or not even having the proper avenues to

salvage, fix or exit the strategy will cause people to panic and just walk away from all of their items. I couldn’t tell you the amount of times that I have done, whether it’s been in a state or whether it’s just been a foreclosure, that people just leave all of their stuff out of the shame and embarrassment of the process of it and the loss is so overwhelming that they just walk out and leave things that you know.

they wouldn’t want to do that and they just don’t see a way out of it. So I come in at a very pivotal point in the very beginning. For instance, the house that I purchased, the woman’s sister had passed away and a realtor friend from school called me and said, hey, I have a clean out. Could you come meet with me? And we can walk through it. And when we did, I kind of…

I asked a little information. I was very interested in purchasing a home anyway. And from the information he gave me, I immediately ran some numbers for the neighborhood, for the ARV. And I was like, you know, I could make this happen. You know, I’m just the first person in the door. It hasn’t been listed yet. All of those things are going to raise how much they’re going to charge for this property. Let me throw an offer in. So for me being in the position that I’m in,

as the first person in the door, I am in a very unique spot. I am one of the first people that even sees it before it’s bare. I got to see the house that I purchased while it still had all of the belongings and build a working relationship with the people that I went up purchasing from during that process, which is always a touchy time. Sometimes they’ve lost someone and people want to be heard. You know, I felt like she was

very much grieving and very much wanted to relive what she was going through with her sister’s belongings that were left. And for me, I am a very, ⁓ I don’t know, let’s say the word emotional person. So it was important for me to not so much worry about the end result as guiding her through what it looks like to start to, how do you say it? I don’t want to say the word throw away because it sounds so awful.

but just get rid of things that meant so much to other people. I mean, you’re going through their personal belongings and you’re deciding what you’re not gonna keep and that’s a very hard situation. So for me, it was really important that they felt listened to and heard throughout the whole process so that we build a relationship that wasn’t gonna be based off whether or not they stole me the house, but it definitely gives you a better, you know, ⁓ a better starting point, a better focal point like, hey,

I hear you, I know what you’re going through and I’m informed on the situation. How can I help you in this situation?

Michelle Kesil (13:25)

Definitely that’s a big role to hold and probably a side of the business most people aren’t familiar with or talking about.

Bobbie (13:36)

Yeah, I feel like it’s it’s like I said, it’s a very unique position and it’s not always an easy position. I mean, it’s never easy. You’re seeing people, you know, who maybe haven’t seen their family for years and years and then now they’re put in a situation where you do have to pick what it is you’re going to keep and what you’re going to do with the home and how you’re going to proceed. And even in fact, you know, some people get caught up in in in the slightest little things, you know, a house can go.

Michelle Kesil (13:43)

short.

Bobbie (14:06)

into foreclosure over a water bill, over a tax bill. You know, for them, it seems so overwhelming. You know, somebody doesn’t even have to pass away. know, Aunt Joan can wind up not paying her water bill or not paying her taxes. The house might be paid off, but her credit could be absolutely awful. She could have no week to week income, no way to even fathom paying a 30 or $50,000 bill.

It could be a half a million dollar property, but with absolutely zero income and zero ability to get that back in good standing again, the risk is just losing the entire property. And sometimes out of shame, people will just do that. They will just walk away and they can’t fix it. So when someone comes in and makes an offer to them, could be a half a million dollar property. You could say, hey, look, I’m going to pay off that bill for you.

And you can always do subject two where you give them the opportunity to pay you. And if they default, you can keep the house or whether you decide to just offer them something to walk away. Some people are just done. And for a quarter of the property’s value, you can offer them that. And they’re in such a situation that they just want to be done with it. They just want to walk away. They want to be free and clear. So you might think you’re getting a deal and in their mind and their heart.

It’s the best thing that could have happened for them because they’re done with it anyway. But it feels so desperate and or embarrassing in the moment that they’re in that sometimes they will just walk away. So I am in a very unique position doing what I’m doing to help and guide people to kind of the next part in their process instead of just giving up and walking away. So it’s almost like a counseling position within. I do pretty well though because I’m a people person, so I enjoy.

Michelle Kesil (15:54)

Yeah. Yeah.

Bobbie (15:59)

the conversation and the story and I want to know what happened and I want to know how you got there and I really enjoy hearing it. I enjoy my job. I tell people that often that I’m sorry to bother. Look, you’re not bothering me. I am. I do this job because I love this job. I do this job because I want to know this is my job. I want to hear about it. Tell me about it, you know?

Michelle Kesil (16:24)

⁓ Amazing.

I’m so happy that you’re able to help people and you’re enjoying the process.

Bobbie (17:12)

Some days it’s not fun. Some days there are hoarder houses and those are just not the funnest. We’ve been in some peculiar situations where you’ve seen the show Hoarders. I’m from Baltimore, that show minimally shows what really can go on out here. ⁓ There are some houses that we go into and I’ve had ones that the fire department has said no.

This is not livable. The health department has shut it down completely. You can’t walk around. They can’t get into if there is an emergency. They couldn’t even begin to get in there and save someone or help someone. And those type of situations are always heartbreaking because truly I don’t think people intend to get that. You know, they don’t intend to be that way. Usually there’s some type of mental issue or mental health issue that’s affiliated with it. And walking them through that process can be.

you know, quite quite intimidating to them. It feels like they’re losing everything even though looks like junk to us. It’s everything to them. You know, it’s all they have. So it’s just a peculiar situation, but I do enjoy it. I do enjoy the the council part of it where you feel like you’re part of the solution.

Michelle Kesil (18:25)

Definitely. What are you most focusing on solving or scaling to next?

Bobbie (18:31)

That’s a couple part. I have a couple contracts that I’ve had for a few years and we’re getting to a point where it’s time to level up on those contracts and that can kind of be intimidating to grow so quickly. I’ve scaled up before and I’ve scaled down. So that can be a little bit intimidating, but I think I enjoy the challenge behind that. Being a female in a male dominated industry gives me a very unique position.

And I also want to work on scaling the houses side of it. I went from beginning to end on this most recent project. And because I had such a, I don’t want to necessarily use the word successful because it doesn’t fit what I’m trying to say, but I had a good experience and it was definitely well-rounded. There are a lot of things that if I could.

go back and change, I probably wouldn’t even change because they taught me some really good lessons. And now that I know I could do this 50, 60, a thousand times, like it’s the learning curve for me. So now I’m gonna do exactly what some people want to do and I’m going to scale larger. I wanna buy multi-units, I wanna buy some apartment buildings. I’d like to get more involved with some ground up projects. I’ve not seen one of them.

in person come to fruition and I’d love to do that. ⁓ I have a couple people who I’ve asked to partner with to do that and they tell me no. And it’s because they’re my friends that they tell me no. ⁓ I’ve asked, I asked with the property I was at now, I said, somebody partner with me. I’ll literally follow you around. You know, I’ll put down all the money. I don’t need you to put in any money. I just need to see what it is you do. Like if you show me. And they all said no, we’re not doing that.

And the reason why is because they knew I could do it on my own and I was just nervous. So they were like nervousness and excitement look very similar Bobbie. They feel the same, but they’re very different. So you’re not nervous. You’re excited, you know, do it and we’re here to guide you. And they did. So it’s going to be the same thing with the ground up projects. I would love to get into brand new builds and, and start to experience that a little more. So that’s definitely on my to-do list.

Michelle Kesil (20:54)

That’s amazing and so exciting that you’re able to take those next steps.

Bobbie (21:00)

I’m very

excited, I’m very excited. This has definitely been a journey and me five years ago couldn’t have imagined accomplishing the things I’m accomplishing now. And now it just seems like such a small thing that it’s gonna be such a larger thing that I’m sure in five more years I’m gonna look back and say, couldn’t have imagined. So I’m excited for that part of my journey.

Michelle Kesil (21:22)

Yeah, what are you most excited about?

Bobbie (21:24)

limited on time, so I won’t go down the rabbit hole. But I come from a very, ⁓ not great place. You know, I grew up in a really bad environment with not a great education because of my home life. And I have achieved so much in, ⁓ in my life. I have gotten to positions that I never even dreamt of. I didn’t dream of them because they didn’t even know they were possible. And I have

three children and ⁓ My my daughters are Well, one of them is following me following kind of what I do But it is nice to show them what a strong business woman really looks like, know It is very nice for them to see how independent I can be, you know

I buried my husband six years ago and I’m a widow and I just remember the feeling when that happened that my whole world had kind of

crumbled around me and what I knew wasn’t going to exist anymore. had been married for 20 years, my entire adult life. And that person that I was when he passed away is nothing like the person that I am now. I found strength within myself that I never knew was possible and I thrived.

You know, it’s awful when you lose someone how that feels. But I never imagined the type of way it would strengthen my character inside and let me know.

what a strong leader I really was for my family and how much they relied on my leadership skills.

Michelle Kesil (23:00)

Incredible. So amazing that you were able to do that.

Bobbie (23:02)

⁓ I am very excited and happy about this part of my life. I feel that I have made it to a very pivotal point and everything now is going to strictly rely on how much work I want to put in and I’m ready to do the work. So I’m very excited.

Michelle Kesil (23:17)

Yeah.

Definitely amazing.

Amazing, Bobbie. Well, thank you for sharing all of that. And before we wrap up here, if someone wants to reach out, connect and stay up to what you’re doing, where can people find you and connect with you?

Bobbie (23:41)

Okay, I am on all social media platforms. We’re on Instagram, TikTok, Facebook. The company’s name is Pick It Bare, like the word naked, B-A-R-E. Years ago, my husband thought that was so clever because we make the house naked inside. And so I’ve stuck with that name and our company colors are red and black. So if you see the website, you’ll kind of see that there. My name is Bobbie Evans.

Bobbie Nicole on social media. I answer all the messages that you guys send me. If you have any questions, I have been mentoring a few people. I enjoy answering the questions and conversating about things that I love and the ways that you can get into stuff like this. So if they have any questions, please feel free to message me. I’d love to talk about it.

Michelle Kesil (24:30)

Perfect. Well, I appreciate your time and your story. Thank you for being here.

Bobbie (24:34)

Okay, it was really nice talking to you, Michelle, and thank you for this opportunity.

Michelle Kesil (24:39)

You’re welcome. Likewise. And for the listeners tuning in, if you got value, make sure you’ve subscribed. We’ve got more conversations with operators like Bobbie, who are building real businesses and we’ll see you on our next episode.

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